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Electrochemical Oxidative Ring-Opening Reactions of 2H-Indazoles with Alcohols to Obtain Ortho-alkoxycarbonylated Azobenzenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-17 Zhenlu Shen, Yibin Hu, Xin Liu, Chenglong Feng, Jiaxu Wang, Meichao Li
A strategy for synthesis of azo-derived compounds by electrochemical oxidative ring-opening reactions of 2H-indazoles with alcohols is reported. The reactions are carried out under galvanostatic electrolysis conditions in an undivided cell without the use of transition metal catalysts. On the basis of cyclic voltam¬metry and control experiments, a plausible mechanism for this ring-opening reaction
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Synthesis of 2-amino-3-arylindoles and their fused analogues via intramolecular C-arylation Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-17 Kateřina Žáková, Petra Králová, Miroslav Soural
2-Aminobenzyl cyanide was reacted with nitrobenzenesulfonyl chlorides and alkylated under Mitsunobu or Fukuyama conditions. The resulting intermediates were exposed to basic conditions, which triggered a Truce-Smiles rearrangement, leading to intramolecular C-arylation. This reaction was followed by spontaneous cycloaddition, which yielded 2-aminoindole derivatives. The developed synthetic route represents
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Stereoselective Synthesis of Functionally Rich Spirooctahydroquinoline Oxindoles via Enynamide Cycloisomerisation/[4+2]-Addition Sequence Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-17 Shiva Madavi, Aman Kumar Jha, Sankar Bharani
Creating an expedient method for synthesizing biologically significant functionally rich octahydroquinoline is a highly sought-after yet challenging endeavour. In this report, we document an unprecedented approach to the construction of novel spirooctahydroquinoline oxindole architectures. The reaction proceeds through Pd (II) catalyzed cycloisomerisation and quinine catalyzed [4+2]-addition sequence
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Catalytic Asymmetric Dearomative Arylation of 2‐Naphthols Enabled by o‐Quinone Diimides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-16 Yuan-Yang Li, Fu-Yuan Yang, Meng-Yuan Wu, Lihua Huang, Guang-Jian Mei
The catalytic asymmetric dearomative arylation of 2‐naphthols enabled by the unconventional reactivity of o‐quinone diimides, i.e. the 1,4‐conjugate addition on quinone sp2 hybridized carbon, has been etablished. Under the catalysis of chiral phosphoric acid, various cyclohexaenones bearing an all‐carbon quaternary stereocenter have been prepared with excellent yields and enantioselectivities.
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Recent Progress in Haloalkene Synthesis by Hydrohalogenation (HX = HCl, HBr, HI) of Alkynes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-16 Kento Iwai, Nagatoshi Nishiwaki
Hydrohalogenation of alkynes is one of the fundamental reactions in organic chemistry, as described in textbooks that begins from old time as Reppe’s chemistry. This method, which directly affords haloalkenes in a single step, is attractive from both industrial and academic viewpoints. Despite the long history of this reaction, novel efficient catalysts and regioselective and/or stereoselective controlled
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Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-16 Mingshuai Zhang, Meichen Liu, Yuetong Qiu, Menglin Peng, Zhilai Zhang, Siyu Song, Xue-Bing Chen, Fuchao Yu
A general and efficient synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope broad and good functional group tolerance. Furthermore, the 3‐furylmethyl chromone skeleton shows the potential synthetic application
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Electrochemical Hydroxylation of α‐Bromoacetophenones: Access to α‐Hydroxyacetophenones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-13 Saurabh Singh, Subhasish Ray, Gaurav Shukla, Malkeet Singh, MAYA SINGH
Herein, a new method has been developed for the synthesis of various α‐hydroxyacetophenones via an electro‐oxidation process. It involves electrocatalytic hydroxylation via debromination of C(sp3)‐Br bond. Here, simultaneous breaking of carbon‐bromine (C‐Br) bond and formation of a new carbon‐oxygen (C‐O) bond has been achieved through electrolysis of H2O using binary mixture of water and DMSO. The
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Solvated Electrons: Dynamic Reductant in Visible Light Photoredox Catalysis Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-13 Aslam Shaikh, Puja Singh, Nand Lal
Open shell species are alluring significant attention owing to their unique physiochemical properties in redox chemistry for activating remarkably stable bonds. Solvated electrons are one of them that have been extensively investigated due to their high reduction potential (Ered = ‐2.9 V vs SHE in CH3CN), diverse substrate activation, and promising applications. If the activating species have a larger
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Catalytic Asymmetric Arylations of Ketimines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-13 Kristina Vlahoviček-Kahlina, Marijan Marijan, Mateja Matišić, Matija Gredičak
Arylation of ketimines is the most straightforward strategy for the construction of chiral α‐tertiary amines, important structural motifs in natural products and biologically active compounds. This comprehensive review highlights the achievements in the transition metal‐catalyzed and organocatalyzed asymmetric arylations of ketimines from the seminal report on catalytic asymmetric arylation of ketimines
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Ruthenium(II)‐Catalyzed Enantioselective Synthesis of 1,2‐trans‐Disubstituted PhSO2CF2‐Containing Cyclopropanes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-12 Chengtao Zhao, Tatiana Besset, PHILIPPE JUBAULT
The direct diastereo‐ and enantioselective Ru(II)‐ catalyzed cyclopropanation reaction of alkenes with ((2‐diazo‐1,1‐difluoroethyl)sulfinyl)benzene was described. The desired enantioenriched PhSO2CF2‐cyclopropanes were obtained in high yields with high diastereo‐ and enantioselectivities in the presence of a chiral ruthenium complex Ru(II)‐Pheox (17‐94% yields, >20:1 d.r. and 83:17‐98:2 e.r.). The
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DBU‐Promoted [3 + 2] Cyclization/Retro‐Mannich Cascade Reaction of N‐Aminoisoquinolinium and N‐Aminoquinolinium Derivatives with para‐Quinone Methides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-12 Shaohong Ma, Mingyang Chen, Zifeng Yang, Xiang Liu, Hua Cao
A DBU‐promoted [3 + 2] cyclization/retro‐Mannich cascade reaction of N‐aminoisoquinolinium and N‐aminoquinolinium derivatives with para‐quinone methides has been established employing a C=C double bond cleavage. A broad range of N‐aminoquinolinium salts, N‐aminoisoquinolinium salts, and para‐quinone methides are well tolerated, providing the corresponding rearrangement products. Moreover, scaled‐up
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Regio‐ and Enantioselective Synthesis of Succinimides Bearing All‐carbon Quaternary Centers Using a Chiral Phenanthroline‐Pd Catalyst Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-08 Yudai Kuroiwa, Masafumi Tamura
The synthesis of chiral succinimides bearing all‐carbon quaternary stereocenters at the C3 position is important, but remains challenging. The present work demonstrates conjugate additions with catalysis by a chiral 1,10‐phenanthroline‐Pd complex (L1‐PdCl2) that exhibit complete regioselectivity with a high degree of enantioselectivity. These reactions afford chiral 3,3‐disubstituted succinimides having
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Formal Insertion of a Metal Carbene Complex into a σ‐Carbon‐Carbon bond. Gold‐catalyzed synthesis of 3H‐indoles. Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-08 Dario Allegue, Diego Sampedro, Alfredo Ballesteros, Javier Santamaría
We report here a formal insertion of a metal carbene complex in a single carbon‐carbon bond. This behavior occurs with the participation of an alpha‐imino gold carbene complex, generated from benzofused triazapentalenes or, in a one‐pot procedure, from their 1‐propargyl‐1H‐bentrotriazole precursors, and gold‐catalytically activated ynamides. As the result, 3H‐indole derivatives were obtained, with
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Metal‐Free Assembly of Benzo[e][1,3]thiazin‐4‐ones via PPh3‐Promoted Cyclization of Benzo[c][1,2]dithiol‐3‐ones and Amidines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-07 Xiaobing Liu, Wenxin Lv, Junjie Dong, Zekai Liu, Feng Hu, Chungcheng Zhou, Yao Zhou
A metal‐free cyclization of benzo[c][1,2]dithiol‐3‐ones and amidines is demonstrated herein. Triphenylphosphine was harnessed as the activating reagent to facilitate the ring‐opening of benzo[c][1,2]dithiol‐3‐ones via S‐S bond cleavage. This PPh3‐Promoted cyclization reaction of benzo[c][1,2]dithiol‐3‐ones enabled to forge a diverse array of 1,3‐benzothiazones in good yields with wide substrate scope
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An Electrochemically Driven Oxidative Strecker Reaction via the Unique Hydroxymethyl Radical Intermediate Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-07 Cheng Chen, Cen-Xuan Wang, Guo-Wei Zhang, Ming-Yu Wu, Shun Feng
Alfa‐aminonitriles are versatile and valuable intermediates in pharmaceutical chemistry. Until now, the Strecker reaction has remained the most efficient tool for synthesizing these compounds. Nevertheless, it is only applicable to aldehyde/imine systems and generally needs metal catalysts and external additives. Herein, an electrochemically driven oxidative Strecker reaction strategy was designed
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Preparation of Hetero‐π‐conjugated Compounds by Double Nucleophilic Addition to Haloalkynes and C‐H Cyclization Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-06 Takeshi Hata, Yuta Tatsumi, Yuuki Kanai, Naoto Takahashi, Masayuki Shigeta, Hirokazu Urabe
When a mixture containing 1‐halo‐1‐alkyne, a dinucleophilic agent, and a base (Cs2CO3 or K3PO4) was heated in DMF, regio‐ and stereo‐selective nucleophilic addition of the dinucleophilic agent to the acetylenes occurred. This reaction yielded (Z,Z)‐bis(haloalkene), which subsequently underwent Pd‐catalyzed cyclization through C–H bond activation, resulting in the formation of two‐oxygen‐ or ‐nitrogen‐containing
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Nickel‐Catalyzed Intramolecular Dual Annulation Reaction of Alkyl Nitrile‐Containing 1,2,3‐Benzotriazin‐4(3H)‐ones: A Pathway to Access Diversely Polycyclic Quinazolinone Alkaloids Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-06 Vijaykumar H. Thorat, Yong-Ran Huang, Chao Hao-Yu, Jen-Chieh Hsieh
Herein, we report a nickel‐catalyzed intramolecular dual annulation reaction of alkyl nitrile‐containing 1,2,3‐benzotriazine‐4(3H)‐ones to synthesize polycyclic quinazolinones. This catalytic reaction can construct the core structure of polycyclic quinazolinone alkaloids; therefore, we also apply this reaction as the critical step to access fifteen relevant alkaloids to demonstrate efficacy.
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Enantioselective Synthesis of Five to Eight‐Membered P‐Stereogenic Benzo‐Fused Heterocycles via Copper‐Catalyzed Dynamic Kinetic Resolution Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-06 Xue Wang, Baixue Liu, Lei Ge, Shanbo Hou, Min Liu, Wenqiang Yang
P‐stereogenic benzo‐fused heterocycles is a privileged skeleton due to their outstanding catalytic properties and bioactivities. However, their enantioselective synthesis is still underdeveloped. Here we demonstrate the use of easily accessible racemic H–P(O) compounds as starting materials and commercial chiral N1, N2‐dimethyl‐1,2‐diphenylethane‐1,2‐diamine ligand in combination with Cu(I) catalysts
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Cp*Ir‐Catalyzed Selective C–H Arylation of 2 Pyridones and 1‐Isoquinolinones with Arylsilanes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-06 Tongxu Su, Heng Xu, Yi Dong
A new Cp*Ir‐catalyzed C–H arylation of 1‐isoquinolinone and 2 pyridones to afford 6‐phenylpyridin‐2(1H)‐ones and 3‐phenylisoquinolin‐1(2H)‐ones by using arylsilanes is described in this paper. This protocol offers significant synthetic advantages, including mild reaction conditions, good functional group tolerance, a wide range of substrate applicability, and a concise approach to the core structure
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Synthesis of 3‐Arylazoindoles through Iron(III)‐Catalyzed C‐H Azolation of Indoles and Arylhydrazines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-06 Kun Li, Jin-Qi Zhang, Wei-Cong Liao, Cui Liang, Xiao-Pan Ma, Dong-Liang Mo, Chun-Hua Chen
A variety of functionalized 3‐arylazoindoles were prepared in good to excellent yields through an iron(III)‐catalyzed C‐H azolation of 2‐substituted indoles with arylhydrazines under mild reaction conditions. The reaction underwent an initial TBN‐mediated nitrosation, 1,5‐hydrogen migration, intramolecular condensation, and 1,5‐hydrogen migration over four steps in one pot. A paracyclophane‐derived
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Rhodium(I) Catalyzed Hydroacylation Reactions of Alkenyl Compounds Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-05 Jun Zhao, Yuan-Yi Lu, Rui Wang, Patience Peters, Hong-Shuang Li
Transition‐metal‐catalyzed hydroacylation of unsaturated substrates with aldehydes involving the formyl C(sp2)–H bond activation provides an expedient and efficient access to the carbonyl compounds such as ketones and esters, which are a class of important scaffolds in natural products and in drug development. Recently, extensive attention has been paid to the hydroacylation reactions of the components
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Enantioselective Syntheses of 3,4‐Dihydropyrans Employing Isochalcogenourea‐Catalyzed Formal (4+2)‐Cycloadditions of Allenoates Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-05 Magdalena Piringer, Mario Hofer, Lukas S. Vogl, Peter Mayer, Mario Waser
We herein successfully demonstrate the use of chiral isochalcogenoureas as Lewis Base catalysts for a variety of [4+2]‐cycloaddition reactions of allenoates and different Michael acceptors. In all cases the same structural key‐motive, a dihydropyran with a (Z)‐configurated exocyclic double bond could be accessed as the major regio‐ and diastereoisomer in an enantioselective manner. Furthermore, these
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Electrochemical Site‐selective Alkylation of Tropones via Formal C(sp3)‐C(sp2) Coupling Reaction Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-05 Andrea Brunetti, Mauro Garbini, Nico Gino Kub, Magda Monari, Riccardo Pedrazzani, Chiara Zanardi, Giulio Bertuzzi, Marco Bandini
The first site‐selective electrochemical alkylation of tropones is realized by reacting 2‐acetoxytropones and redox‐active‐esters. The electroreductive protocol enables the preparation of a wide range (27 examples) of mono‐ and disubstituted tropones in high yields (up to 71%) and very mild conditions. Dedicated voltammetric measurements served for the identification of 2‐acetoxytropones as a class
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Cascade Cyclization/Amination of para‐Quinone Methides with β‐Ketodinitriles: Synthesis of Polysubstituted Furans Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-05 Liyong Fan, Longzhi Zhu, Wenli Shang, Mingming Yin, Biquan Xiong, Wuxing Xie, Fan Cao, Yu Liu, Yi Chen, Renhua Qiu
A protocol for the synthesis of trisubstituted furans via phosphoric acid‐catalyzed regioselective cascade cyclization/amination of para‐quinone methides (p‐QMs) with β‐ketodinitriles has been disclosed for the first time. Various kinds of p‐QMs and β‐ketodinitriles can effectively produce the desired polysubstituted furan derivatives in 64‐95% yields, demonstrating high atomic economy and their application
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Tetrafluoropyridinyl thiolate as a tool for enabling photoredox alkylation of 1,2,4‐oxadiazoles Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-05 Alexander Frumkin, Vitalij Levin, Alexander D. Dilman
A method for the radical functionalization of 1,2,4‐oxadiazoles using alkyl halides as precursors of radicals is described. The reaction efficiency is determined by potassium tetrafluoropyridinyl thiolate additive, which plays dual role. First, the thiolate converts alkyl halides into more reactive fluorinated aryl sulfides, which undergo photoredox activation of the C‐S bond. Second, the thiolate
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Photo‐Induced Synthesis of Functionalized γ‐Lactams via Iron‐Catalyzed LMCT Cascade Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-05 Zhuoheng Song, Jinrui Bai, Dan Qi, Lin Guo, Chao Yang, Wujiong Xia
A base‐and‐additive‐free photo‐induced radical‐mediated cascade cyclization reaction of 1,6‐enyne compounds was presented. In this study, C(sp3)‐H hydrocarbons, including various alkanes and ethers, were activated via Fe‐catalyzed photo‐induced conditions, providing a bunch of γ‐lactam products via hydrogen atom transfer and radical addition processes. Control experiments indicated that the reaction
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Synthesis of quinine‐inspired antimalarials by Ni‐catalysed cross electrophile coupling Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-05 Aggie Lawer, Finlay Player, Vicky M Avery, Daniel J Foley
We describe the efficient synthesis of novel dehydroxyquinines by arylation of quincorine bromide using Ni‐catalysed cross electrophile coupling. The method demonstrates robust compatibility with (hetero)aryl bromides bearing diverse functional groups. Oxidation at C‐9 of the dehydroxyquinines expediently provided quinine‐inspired pseudo‐natural products (‘quinalogs’). Investigation of the compound
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Gold‐Catalyzed Synthesis of Ortho‐Quinone Methide Analogues as Reactive Synthetic Precursors Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-05 Tsuyoshi Yamada, Akiko Fujii, Chikara Furugen, Kwihwan Kobayashi, Tomoki Hyodo, Takashi Ikawa, Hironao Sajiki
2‐Exomethylene indolin‐3‐ones are useful synthetic intermediates with a unique indole scaffold. However, their synthesis has not yet been reported owing to their reactivity and instability. In this study, a gold(I)‐catalyzed method for generating 2‐exomethylene indolin‐3‐one derivatives via the 5‐exo‐dig‐selective cyclization of 2‐(2‐amino)phenyl alkynyl ketones with an alkyne terminus was developed
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Gold‐Catalyzed Tandem Oxidation–Migration of 3‐Propargyl Indoles: Synthesis of α‐Indol‐3‐yl α,β‐Unsaturated Carbonyls Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-02 Lorena Renedo, Estela Álvarez, Marta Solas, Samuel Suárez-Pantiga, Manuel Ángel Fernández-Rodríguez, Roberto Sanz
α‐Indol‐3‐yl α,β‐unsaturated carbonyl compounds are synthesized from 3‐propargyl indoles, obtained by direct propargylation of indoles, via a gold‐catalyzed tandem oxidation–1,2‐indole migration reaction in the presence of pyridine N‐oxides. Fine‐tuning of the catalyst and oxidant enables the reaction of 3‐propargyl indoles bearing different substituents. The order of oxidation and indole migration
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Electrochemical trifluoromethylalkoxylation of endocyclic enamides in batch and flow Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-02 Elise Leclercq, wael Barakat, Radhouan Maazaoui, Mael Penhoat, Isabelle Gillaizeau, Laetitia Chausset-Boissarie
A regioselective electrochemical oxytrifluoromethylation of endocyclic enamides is reported. The 1,2‐difunctionalization proceeds under mild conditions in an undivided cell and employs the inexpensive bench stable Langlois’ reagent. This novel environmentally friendly multicomponent strategy gives access to a wide range of α,β‐substituted amines by means of various alcohols as nucleophiles in high
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Ruppert‐Prakash Reagent (TMSCF3)‐Catalyzed Chemoselective Esterification of Weinreb Amides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-02 Margherita Miele, Laura Castoldi, Egle Beccalli, Vittorio Pace
A straightforward TMSCF3‐catalyzed conversion of Weinreb amides into esters through the treatment with sodium alkoxides is reported. The procedure documents a genuine selectivity for the esterification of primary alcohols with Weinreb amides featuring diverse substitution pattern. The constitutive N‐methoxy fragment of these acylating agents is responsible for the unique reactivity they display, thus
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Ball‐milling to access dinucleoside polyphosphates and analogues Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-02 Valentin Navarro, Florian Vasco, Xavier Bantreil, Frederic Lamaty, Suzanne Peyrottes, Béatrice Roy
Dinucleoside 5’,5’‐polyphosphates (NpnNs) play essential roles in various biological processes. Access to these high value‐added compounds, while avoiding the many drawbacks of solution phase synthesis, is a challenge that has been overcome thanks to mechanochemistry. A straightforward solid‐state synthesis based on activation of phosphate or pyrophosphate sodium salts to their diimidazolides, followed
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A solely‐Fe‐catalyzed Sonogashira‐type coupling of non‐activated secondary alkyl iodides with terminal alkynes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-01 Guillaume Lefèvre, Fedor Zhurkin, William Parisot
An iron‐catalyzed Sonogashira coupling of non‐activated secondary alkyl iodides with terminal alkynes is described. The reaction proceeds under mild conditions in N‐MethylPyrrolidone without auxiliary ligand or co‐catalyst. This procedure allowed the obtention of 28 coupling products. Moreover, slow addition of LiHMDS base allows to achieve up to 89% yields. This method enables the conversion of non‐activated
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Visible Light catalyzed Stannylation of Aryl Halides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-01 Di Qiu, Qianhang Ren, Guanglu Yue, Maurizio Fagnoni, Stefano Protti
A visible light‐mediated strategy for the preparation of aromatic stannanes from aryl halides (mostly aryl bromides) is presented herein. The reaction proceeds under metal‐ and additive‐free conditions and exhibits a broad substrate scope. The products obtained have been employed in the C‐C bond formation via Stille cross‐coupling reactions. Mechanistic investigation evidenced the key role of both
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Recyclable Iridium Catalyst Supported on Porous Organic Polymer for Acceptorless Dehydrogenative Silylation: Synthesis of Ring‐Fused Oxasilacycles Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-01 Jiayi Xian, Xing Sheng, Yi Lin, Zhenning Sun, Chaohan Chen, Kun Zhou, Chao Peng, Bin Li, Xiuwen Chen, Feng Xie
The direct conversion of specific C–H bonds to C–Si bonds in alkanes or aromatics via catalytic methods has attracted growing research interest. Herein, we report the preparation of a new iridium catalyst supported on a naphthyridine‐based porous organic polymer and its successful application in the dehydrogenative silylation of 2‐arylphenols or alcohol and hydrosilanes to access ring‐fused oxasilacycles
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Photoredox Radical Cascade Cyclization of 2‐Alkynylarylnitriles in Visible Light: Direct Access to 3‐Amino‐1‐indenones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-01 Shruti Rajput, Dikshita Garg, Nidhi Jain
A photoinduced direct synthesis of 3‐amino‐1‐indenones via radical cascade cyclization strategy is demonstrated. The methodology involves a domino reaction between 2‐alkynylarylnitrile and N‐aminopyridinium salt and captures the reactivity of in‐situ generated nitrogen‐centered radical (NCR) in visible light. Multiple bond‐forming events including C‐N, C‐C, and C‐O take place sequentially on 2‐alkynylarylnitrile
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Access to tetrahydrothiopyrano[2,3‐b]indole derivatives via zinc‐catalyzed asymmetric [3 + 3] annulation of indoline‐2‐thiones with yne‐enones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-01 Dan-Dan Cui, Jian-Wen Shi, Tong Wang, Yuan-Zhao Hua, mincan wang, Guang-Jian Mei, Jun-Long Niu, Shikun Jia
We report herein an enantioselective [3 + 3] annulation of indoline‐2‐thiones with yne−enones by chiral dinuclear zinc catalysts via a Brønsted base and Lewis acid cooperative activation. This transformation proceeded through sequential conjugate addition, allenyl ketone formation and intramolecular sulfa‐Michael 6‐endo‐trig cyclization. A range of enantioenriched tetrahydrothiopyrano[2,3‐b]indole
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Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-29 Rekha Sangwan, Zanjila Azeem, Pintu Kumar Mandal
Recently, C‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids as well as in pharmaceutically active molecules. Because of the stability and great utility of C‐glycosides, synthetic approaches en route to the C‐C bond formation have gradually become a center of attraction in carbohydrate chemistry. Towards these researches, C‐glycosylation with heteroaryl
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Synthesis of Spiroindolenines by Iodine‐Mediated Dearomative Aza‐Spirocyclization of Indoles Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-29 Zongxiang Zhao, Huilin Qiu, Junbiao Chang, Wenquan Yu
A transition‐metal‐free dearomative aza‐spirocyclization reaction of 2,3‐disubstituted indoles is established by using molecular iodine under basic conditions. The required substrates were prepared via sequential Fisher indole synthesis and sulfonylation. This dearomatization reaction is amenable to gram‐scale synthesis, and provides access to various spiroindolenine derivatives from indole sulfonamide
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BF3·OEt2 and Visible Light‐Controlled [3,3]‐ or [1,3]‐Rearrangement of Quinazolinone N‐O Aryl Moieties Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-29 Shu-Min Nie, Lu-Min Cheng, Chun-Hua Chen, Cui Liang, Cheng-Xue Pan, Dong-Liang Mo
We described a base‐promoted O‐arylation of N3‐hydroxyl quinazolinones with diaryliodonium salts and sequential BF3·OEt2 and visible light‐controlled [3,3]‐ or [1,3]‐rearrangements of quinazolinone N‐O aryl moieties to prepare a variety of 2‐(quinazolin‐4‐yloxy)phenols and atropisomeric 3‐(2‐hydroxyphenyl)quinazolin‐4‐ones in 44%‐75% yields and 28%‐70% yields, respectively. Mechanistic studies showed
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Asymmetric Synthesis of 3,4‐Dihydroquinolin‐2‐ones via Organocatalytic [4+2]‐Cyclization of 2‐Amino‐β‐nitrostyrenes with Azlactones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-29 Heebum Kim, Yeongju Kim, Sung-Gon Kim
Dihydroquinolin‐2‐ones, recognized for their significant bioactive properties, feature a unique six‐membered structure with nitrogen‐containing heterocycles. A breakthrough method has been developed to synthesize enantioenriched 3,4‐dihydroquinoline‐2‐one derivatives. This innovative approach utilizes an asymmetric [4+2]‐cyclization process, combining 2‐amino‐β‐nitrostyrenes with azlactones, and is
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Visible Light Induced Photocatalyst‐Free C‐X (X = B, C, O, P, S, Se) Bond Formation of Aryl Halides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-29 Jitender Singh, Nihal Singh, Anuj Sharma
Aryl halides are one of the most important chemical feedstocks in pharmaceuticals due to its easy accessibility, inexpensiveness, and widely utilized as aryl radical precursors in organic synthetic chemistry. Conventionally, the stoichiometric reagents such as AIBN/n‐Bu3SnH were used for generation of aryl radical from aryl halides, and suffered from requirement of toxic radical initiators, high temperature
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Room‐Temperature Synthesis of α‐Alkylated Indolin‐2‐ones via a Photo Assisted Iron Catalyzed Borrowing Hydrogen Reaction Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-29 Dingguo Song, Rong Chen, Weiwei Huang, Pengtao Yang, Lingxin Chen, JiaLin Zhang, Fei Ling, Weihui Zhong
Alcohols and oxindoles derivatives are highly important skeletons, widely applicated in both organic and bioorganic chemistry. Herein, we reported a visible‐light‐induced iron‐catalyzed α‐alkylation of oxindoles with alcohols to offer a variety of α‐alkylled oxindoles at room temperature. This reaction featured broad substrate scope with good functional tolerance under simple conditions. Detailed mechanistic
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Organophotocatalytic Carbamoylation of Morita‐Baylis‐Hillman Carbonates Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-29 Lucas Marchini, Jeimy Vélez, Elias Andre, José Tiago, Sidnei Moura, Márcio Paixão
The synthesis and modification of structures containing the amide functionality play a significant role in the development of pharmaceuticals and biologically active compounds. While conventional amidation strategies primarily relies on C‐N bond formation, the strategic integration of photoredox catalysis for synthesizing these compounds through C‐C bond formation is in accordance with the principles
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Catalytic Synthesis of Atropoisomers via Non‐canonical Friedel‐Crafts Reactions Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-29 Xutong Ye, Xixiang Yu, Rui Deng, Fangrui Zhong, Guojiao Wu
The Friedel‐Crafts reaction stands as a powerful synthetic tool for C‐H functionalization of aromatic feedstocks, which is conventionally realized through electrophilic alkylation and acylation. The burgeoning interests in axially chiral compounds across diverse fields have spurred extensive exploration of this classic transformation for catalytic atroposelective synthesis. Consequently, the past decade
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Special Issue Dedicated to Miquel A. Pericàs Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-27 Montserrat Diéguez, Andreas Pfaltz, Antoni Riera
This special issue of Advanced Synthesis and Catalysis is dedicated to Miquel Àngel Pericàs i Brondo to pay tribute to his distinguished scientific career and his eminent achievements as a founder and director of the Institute of Chemical Research of Catalonia (ICIQ), which under his leadership has developed into a world-class center for organic synthesis and catalysis. This Special Issue collects
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Miquel Pericàs and the Creation of ICIQ Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-27 Ernesto Carmona, Javier de Mendoza, Luis A. Oro
The distinguished research career of Professor Miquel Pericàs started in the mid-1970s and has provided him with a well-deserved international reputation. This becomes evident in this issue of Advanced Synthesis and Catalysis with the scientific contributions that many colleagues with a personal or professional connection to Miquel have dedicated to him. In the present brief note we highlight the essential
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Miquel Pericàs – an Outstanding Scientist and a Great Friend Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-27 Stephen L. Buchwald
From left to right: Miquel Pericàs, Laura Herrero (Ruben Martin's wife), Anne-Liese Pericàs, Steve Buchwald, Ruben Martin I first met Miquel Pericàs when he came to MIT to visit in the mid-1990s and to check on the progress of his student, Xevi Verdaguer, who was a postdoc with me. Little did I know that this would be the beginning of a close personal and professional relationship that has now gone
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Front Cover Picture: Organocatalytic Enantioselective Syntheses of Flavonoids and Cannabinoids (Adv. Synth. Catal. 5/2024) Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-27 Andreu Vidal-Albalat, Bruno Matos Paz
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Development of Cyanopyridazine Derivatives as Photoredox Catalysts and Evaluation of their Catalytic Performance Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-26 Yinhong Tang, Yan Liu, Peng Zhu, Junsen Pang, Yungui Peng
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One-Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-26 Hong-Gon Kim, Youngho Jang, Jong-Shik Shin
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Enabling C7 Methylation and Arylation of the Indolyl Core via P(III)-Directed C−H Functionalization Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-25 Christopher B. Kelly, Rosaura Padilla-Salinas, Wenyong Chen, Mikko Muuronen, Jaume Balsells
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The Asymmetric Synthesis of Polycyclic Tetrahydroxanthone via the Cascade Reaction of Alkene-Substituted 1,3-diketones and Alkenyloxindoles Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-25 Rong Zhang, Wenhui Wang, Yonghui Zhang, Yushuang Chen, Weijun Yao, Zhen Wang
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Oxidative Alkenylation of (Hetero)aromatics with Unactivated Alkenes: Control of the Reaction Selectivity Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-23 Chenhui Hu, Keyu Xiang, Tao Ying, Jingbo Yu
Alkenylbenzene skeletons represent one of the most widely occurring structural motifs in pharmaceutical drugs, natural products, and advanced materials. The construction of alkenylbenzenes is promising through the use of a straightforward oxidative alkenylation protocol, particularly from unactivated alkenes. This is significant because unactivated alkenes are inexpensive raw materials that can be
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Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium-Catalyzed Synthesis of Phenanthrenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-22 Xiao Liu, Bingxin Zhou, Kelu Yan, Jiangwei Wen, Qiuyun Li, Xutong Wang, Xiu Wang
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Catalytic Generation and Intermolecular Addition of Diarylmethyl Anions Utilizing [1,2]-Phospha-Brook Rearrangement Under Brønsted Base Catalysis Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-21 Azusa Kondoh, Masahiro Terada
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Front Cover Picture: Special Issue Dedicated to Miquel A. Pericàs (Adv. Synth. Catal. 4/2024) Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-21 Montserrat Diéguez, Andreas Pfaltz, Antoni Riera
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Regioselective [3+2]-Spiroannulation and [4+n]-Annulation Approaches through Activation of C−H Bond Facilitated by Ru(II) as Catalyst: Role of Solvent Selectivity Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-20 Rahul Dev Mandal, Anindita Sarkar, Dwaipayan Das, Asish R. Das
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Synthesis of Difluorocyclopropanes via Visible-Light-Mediated [1+2] Cycloaddition of Diazo Esters with gem-Difluoroalkenes and Evaluation of their Antifungal Activity Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-16 Donghua Du, Chang Ji, Shaoying Zheng, Yu Chen, Huanyu Cai, Zhenghua Li, Dingce Yan, Huailong Teng
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Catalytic Orthogonal Glycosylation Enabled by Enynal-Derived Copper Carbenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-02-16 Surya Pratap Singh, Bidhan Ghosh, Indrajeet Sharma