-
Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Jiupeng Liu, Shuo Tang, Shichong Wang, Mengting Cao, Jingjing Zhao, Puyu Zhang, Pan Li
-
Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions Org. Lett. (IF 6.005) Pub Date : 2022-06-24 Alexander Kazantsev, Olga Bakulina, Dmitry Dar’in, Grigory Kantin, Alexander Bunev, Mikhail Krasavin
-
Chiral Counteranion-Directed Catalytic Asymmetric Methylene Migration Reaction of Ene-Aldimines J. Org. Chem. (IF 4.354) Pub Date : 2022-06-23 Norie Momiyama, Chanantida Jongwohan, Naoya Ohtsuka, Pawittra Chaibuth, Takeshi Fujinami, Kiyohiro Adachi, Toshiyasu Suzuki
-
SN2 versus SN2′ Competition J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Thomas Hansen, Pascal Vermeeren, Lea de Jong, F. Matthias Bickelhaupt, Trevor A. Hamlin
We have quantum chemically explored the competition between the SN2 and SN2′ pathways for X– + H2C═CHCH2Y (X, Y = F, Cl, Br, I) using a combined relativistic density functional theory and coupled-cluster theory approach. Bimolecular nucleophilic substitution reactions at allylic systems, i.e., Cγ═Cβ–Cα–Y, bearing a leaving-group at the α-position, proceed either via a direct attack at the α-carbon
-
Porphyrindiene-Based Tandem Diels–Alder Reaction for Preparing Low-Symmetry π-Extended Porphyrins with Push–Pull Skeletons J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Guanyue Cao, Glib Baryshnikov, Chen Chen, Liyuan Chen, Tengjiao Zhao, Shuyi Fu, Zhenhui Jiang, Xiujun Liu, Qizhao Li, Yongshu Xie, Chengjie Li
-
TEMPO-Promoted Mono- and Bisimidation of Tertiary Anilines: Synthesis of Symmetric and Unsymmetric N-Mannich Bases J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Xiu Juan Xu, Adila Amuti, Wen Jing Hu, Qiaerbati Adelibieke, Abudureheman Wusiman
-
Heptagon-Embedded π-Expanded Thieno- and N-Methylpyrrolo-Pyridazines with Substantial Out-of-Plane Dipole Moment J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Masato Hisada, Daiki Shimizu, Kenji Matsuda
-
One-Pot Synthesis of α-Amino Bisphosphonates from Nitriles via Tf2O/HC(OR)3-Mediated Interrupted Ritter-Type Reaction J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Ya-Cheng Hong, Jian-Liang Ye, Pei-Qiang Huang
A versatile synthesis of α-amino bisphosphonates has been achieved through one-pot interrupted Ritter-type reaction under mild conditions. The reactive Ritter intermediate nitrilium is in situ generated by treatment of nitrile with readily accessible Tf2O/HC(OR1)3, which is trapped by phosphite ester to deliver the desired product. This protocol is efficient, scalable, and well compatible with a broad
-
Enantioselective Friedel–Crafts Reaction of 2-Alkynyphenols with Aromatic Ethers by Chiral Brønsted Acid Catalysis J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Wenxuan Zhang, Jiaying Sun, Zhendong Lian, Ran Song, Daoshan Yang, Jian Lv
-
Stabilization of Glucosyl Dioxolenium Ions by “Dual Participation” of the 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Protection Group for 1,2-cis-Glucosylation J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Wouter A. Remmerswaal, Kas J. Houthuijs, Roel van de Ven, Hidde Elferink, Thomas Hansen, Giel Berden, Herman S. Overkleeft, Gijsbert A. van der Marel, Floris P. J. T. Rutjes, Dmitri V. Filippov, Thomas J. Boltje, Jonathan Martens, Jos Oomens, Jeroen D. C. Codée
The stereoselective introduction of glycosidic bonds is of paramount importance to oligosaccharide synthesis. Among the various chemical strategies to steer stereoselectivity, participation by either neighboring or distal acyl groups is used particularly often. Recently, the use of the 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) protection group was shown to offer enhanced stereoselective steering
-
Enantioselective Conjugate Addition of Boronic Acids to α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Chiral Diols J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Guo-Li Chai, Ping Zhang, En-Ze Yao, Junbiao Chang
-
Phospha-Michael Addition on α-Fluorinated Acrylates: A Straightforward Access to Polyfunctionalized Fine Chemicals J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Xin Huang, Tatiana Besset, Philippe Jubault, Samuel Couve-Bonnaire
-
Straightforward Synthesis of Alkyl Fluorides via Visible-Light-Induced Hydromono- and Difluoroalkylations of Alkenes with α-Fluoro Carboxylic Acids J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Chunfang Guo, Xuliang Han, Yu Feng, Zhaolong Liu, Yueyun Li, Hui Liu, Lizhi Zhang, Yunhui Dong, Xinjin Li
-
Regioisomerism in Symmetric Dimethyl Dialdehydes Dictates their Photochemical Reactivity J. Org. Chem. (IF 4.354) Pub Date : 2022-06-24 Florian Feist, Leona L. Rodrigues, Sarah L. Walden, Christopher Barner-Kowollik
-
Importance of Green and Sustainable Chemistry in the Chemical Industry Org. Process Res. Dev. (IF 3.317) Pub Date : 2022-06-23 Juan Colberg, King Kuok (Mimi) Hii, Stefan G. Koenig
This article references 14 other publications. This article has not yet been cited by other publications. This article references 14 other publications.
-
Pocahemiketone A, a Sesquiterpenoid Possessing a Spirocyclic Skeleton with a Hemiketal Endoperoxide Unit, Alleviates Aβ25–35-Induced Pyroptosis and Oxidative Stress in SH-SY5Y Cells Org. Lett. (IF 6.005) Pub Date : 2022-06-24 Qin-Mei Zhou, Hao-Yu Zhao, Chuan Ma, Lu Huang, Jie Liu, Li Guo, Cheng Peng, Liang Xiong
-
Synthesis of 2-Phospha[7]helicene, a Helicene with a Terminal Phosphinine Ring Org. Lett. (IF 6.005) Pub Date : 2022-06-24 Tomáš Beránek, Martin Jakubec, Jan Sýkora, Ivana Císařová, Jaroslav Žádný, Jan Storch
-
Synthesis of Unnatural α-Amino Acid Derivatives via Photoredox Activation of Inert C(sp3)–H Bonds Org. Lett. (IF 6.005) Pub Date : 2022-06-24 Florence Babawale, Kathiravan Murugesan, Rok Narobe, Burkhard König
-
Aspcandine: A Pyrrolobenzazepine Alkaloid Synthesized by a Fungal Nonribosomal Peptide Synthetase-Polyketide Synthase Hybrid Org. Lett. (IF 6.005) Pub Date : 2022-06-24 Lin Chen, Jian-Wei Tang, Yan Yee Liu, Yudai Matsuda
-
Silver-Catalyzed Carbon Dioxide Fixation on Alkynylindoles Org. Lett. (IF 6.005) Pub Date : 2022-06-24 Seiya Uema, Kodai Saito, Tohru Yamada
-
Palladium-Catalyzed Desulfonative Carbonylation of Thiosulfonates: Elimination of SO2 and Insertion of CO Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Jian-Xing Xu, Le-Cheng Wang, Xiao-Feng Wu
-
Recent Advances in the Transformations of Different Types of Stemona Alkaloids Org. Chem. Front. (IF 5.281) Pub Date : 2022-06-24 Tao Shi, Xiaodong Wang, Jin hong Chen, Fei Cao, Gaofeng Yin, Yao-Fu Zeng, Zhen Wang
In recent years, researches on the total syntheses of Stemona alkaloids with different 5/7 bicyclic systems have attracted increasing attention, and the development momentum in this field has gradually changed from single molecule synthesis to unified syntheses of multiple molecules. Among them, the emergence of mutual transformations among Stemona alkaloids with different ring systems has indeed improved
-
Functionalized Cyclopentenes via the Formal [4+1] Cycloaddition of Photogenerated Siloxycarbenes from Acyl Silanes J. Org. Chem. (IF 4.354) Pub Date : 2022-06-23 João R. Vale, Rafael F. Gomes, Carlos A. M. Afonso, Nuno R. Candeias
-
A Visible Light Ru-Catalyzed Photoredox Access to Substituted Dihydrofurans J. Org. Chem. (IF 4.354) Pub Date : 2022-06-23 Jorge Victoria-Miguel, William H. García-Santos, Alejandro Cordero-Vargas
-
Deracemization of Binaphthyl by Suzuki Diarylation: The Role of Electronic and Steric Effects J. Org. Chem. (IF 4.354) Pub Date : 2022-06-23 Filip Bulko, Michal Májek, Martin Putala
-
Process Intensive Synthesis of Propofol Enabled by Continuous Flow Chemistry Org. Process Res. Dev. (IF 3.317) Pub Date : 2022-06-23 Laurent Vinet, Lorenzo Di Marco, Vanessa Kairouz, André B. Charette
-
Development and Scale-Up of a Copper-Catalyzed Sulfamidation Coupling Reaction Org. Process Res. Dev. (IF 3.317) Pub Date : 2022-06-23 Neil K. Adlington, Paul S. Siedlecki, Ian Derrick, Simon D. Yates, Andrew D. Campbell, Paula Tomlin, Thomas Langer
-
Weakly Coordinating tert-Amide-Assisted Ru(II)-Catalyzed Synthesis of Azacoumestans via Migratory Insertion of Quinoid Carbene: Application in the Total Synthesis of Isolamellarins Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Souradip Sarkar, Rajarshi Samanta
-
Thiocyanatoarylation of Methyl Vinyl Ketone under Meerwein Conditions for the Synthesis of 2-Aminothiazole-Based Heterocyclic Systems Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Yurii V. Ostapiuk, Oksana V. Barabash, Mary Y. Ostapiuk, Evgeny Goreshnik, Mykola D. Obushak, Andreas Schmidt
4-Aryl-3-thiocyanatobutan-2-ones were prepared by Meerwein reactions from methyl vinyl ketone and aryldiazonium salts under copper(II) catalysis in 35–75% yields. α-Thiocyanato ketones regioselectively react with 1-methyl-3-aminopyrazole forming N-(3-pyrazolyl)-substituted 2-aminothiazoles in 80–91% yields. An ester group in position 3 of the pyrazole induced a regioselective ring-closure reaction
-
Highly Substituted Acephenanthrylenes and Their π-Extended Derivatives: Syntheses, Structural Analyses, and Properties Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Po-Ting Chen, Chia-Ling Yu, Min-Hsiu Shen, Mu-Jeng Cheng, Yao-Ting Wu, Hsiu-Fu Hsu
-
Combinatorial Biosynthesis of Terpenoids through Mixing-and-Matching Sesquiterpene Cyclase and Cytochrome P450 Pairs Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Man-Cheng Tang, Cheng Shen, Zixin Deng, Masao Ohashi, Yi Tang
-
Homoallylboration of Aldehydes: Stereoselective Synthesis of Allylic-Substituted Alkenes and E-Alkenes Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Daniel Polyak, Bokai Xu, Isaac J. Krauss
-
A Mechanistic Switch from Homoallylation to Cyclopropylcarbinylation of Aldehydes Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Woojin Lee, Daniel Polyak, Bokai Xu, K. N. Houk, Isaac J. Krauss
-
Catalytic Enantioselective Reductive Cross Coupling of Electron-Deficient Olefins Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Kangning Cao, Chunyang Li, Dong Tian, Xiaowei Zhao, Yanli Yin, Zhiyong Jiang
-
Correction to “Synthetic Studies toward DNA-Encoded Heterocycles Based on the On-DNA Formation of α, β-Unsaturated Ketones” Org. Lett. (IF 6.005) Pub Date : 2022-06-23 Sixiu Liu, Jingjing Qi, Weiwei Lu, Xuan Wang, Xiaojie Lu
The affiliation of the corresponding author Xiaojie Lu was incorrect. Previously published affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Zhang Jiang Hi-Tech Park, Pudong, Shang-hai, 201203, China Corrected affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy
-
Bromine-Radical-Induced Csp2-H Difluoroalkylation of Quinoxalinones and Hydrazones through Visible-Light-Promoted Csp3-Br Bond Homolysis Org. Chem. Front. (IF 5.281) Pub Date : 2022-06-23 Chuanhua Qu, Run Huang, Yuan Liu, Tong Liu, Guiting Song
Disclosed herein is a photosensitizer-free strategy for the direct C-H difluoroalkylation of quinoxalinones and hydrazones with bromodifluoroacylarenes via visible-light-promoted Csp3-Br bond homolytic pathway. This new reaction provides the access to difluoroalkylated quinoxaline and hydrazone derivatives with excellent substrate generality under simple, mild, green, and metal-free conditions. This
-
Triton B-promoted regioselective intramolecular addition of enolates to tethered ynamides for the construction of 8-membered O-heterocycles Org. Chem. Front. (IF 5.281) Pub Date : 2022-06-18 Santanu Ghosh, Yongxiang Zheng, Daniele Maccarone, Feven-Alemu Korsaye, Ilaria Ciofini, Laurence Miesch
-
Nickel-Catalyzed Tandem Ring Contraction of TEMPO and C-N Bond Transamination of Enaminones toward Amino Diversity of Enaminones Eur. J. Org. Chem. (IF 3.021) Pub Date : 2022-06-22 Haozhi Wu, Tian Luo, Jie-Ping Wan, Jianwen Jiang, Yunyun Liu
The reactions of N,N -substituted enaminones with TEMPO leading to the synthesis of 2,2-dimethyl pyrrolidine functionalized new enaminones have been established by Ni(II) catalysis. Interesting ring contraction on TEMPO as well as the enaminone C-N bond amination bring new tool for generating molecular diversity of enaminones in the amino group fragment.
-
Palladium-Catalyzed Activation of Carbon–Halogen Bonds: Electrostatics-Controlled Reactivity Eur. J. Org. Chem. (IF 3.021) Pub Date : 2022-06-22 Bryan Phuti Moloto, Pascal Vermeeren, Marco Dalla Tiezza, Catharine Esterhuysen, F. Matthias Bickelhaupt, Trevor A. Hamlin
We have quantum chemically studied the palladium-mediated activation of C(spn)–X bonds (n = 1–3; X = F, Cl, Br, I) in the archetypal model substrates H3C–CH2–X, H2C=CH–X, and HC≡C–X by a model bare palladium catalyst, using relativistic density functional theory at ZORA-BLYP/TZ2P. The bond activation reaction barrier decreases, for all sp-hybridized carbon centers, when the substituent X of the substrate
-
Dual Metallaphotoredox Catalyzed Directed C(sp2)-H Functionalization: Access to C-C/C-Heteroatom Bonds Eur. J. Org. Chem. (IF 3.021) Pub Date : 2022-06-22 Tanumay Sarkar, Tariq A. Shah, Prabhat Kumar Maharana, Bijoy Debnath, Tharmalingam Punniyamurthy
Metallaphotoredox catalysis represents the combination of two activation modes, viz; metal-catalyzed C-H functionalization and visible-light-induced photocatalysis. This appealing dual catalysis technique has evolved as a versatile platform that has paved the way for diverse low-energy pathways for a plethora of synthetic transformations. The synergistic combination of two “green” approaches has garnered
-
Synthesis of Thioalkynes by Desilylative Sonogashira Crosscoupling of Aryl Iodides and 1-Methylthio-2-(trimethylsilyl)ethyne Eur. J. Org. Chem. (IF 3.021) Pub Date : 2022-06-22 Yang Cao, Yang Huang, Paul R. Blakemore
1-Methylthio-2-arylethynes were prepared in typically good to excellent yields from aryl iodides and 1-methylthio-2-(trimethylsilyl)-ethyne by a desilylative Sonogashira process employing Pd(PPh 3 ) 2 Cl 2 (1 mol%), CuI (10 mol%), and K 2 CO 3 (6 eq) in MeOH-Et 3 N-THF (1:2:2) at rt for 16 h (16 examples, 31-96% yield). Thienyl and pyridyl iodides (all regioisomers) were similarly converted to 1-m
-
Access to Sulfocoumarins via Three-Component Reaction of β-Keto Sulfonyl Fluorides, Arynes, and DMF Eur. J. Org. Chem. (IF 3.021) Pub Date : 2022-06-21 Yuan Huang, Xueyan Zhao, Dengfeng Chen, Yu Zheng, Jinyue Luo, Shenlin Huang
Sulfonyl fluorides have found diverse applications in multiple disciplines due to their reactivity and stability. Thus, exploiting the new reactivity of sulfonyl fluorides is of high importance to Sulfur (VI) Fluoride Exchange (SuFEx) chemistry. Reported herein is a three-component reaction of β-keto sulfonyl fluorides, arynes and DMF for the streamline synthesis of sulfocoumarins. The reaction proceeds
-
Organocatalytic Synthesis of Thiiranes from Alkenes Eur. J. Org. Chem. (IF 3.021) Pub Date : 2022-06-21 Anna Tsoukaki, Elpida Skolia, Christoforos G. Kokotos
Thiiranes, the corresponding sulfur analogues of epoxides, are less studied and less encountered in literature. This might be due to the limited existing synthetic approaches for their synthesis. Herein, a mild, sustainable and efficient organocatalytic synthesis of thiiranes has been developed. Starting from olefins and utilizing the epoxidation protocol developed in the Kokotos’ group, which employs
-
Flexible Approach for the Synthesis of Annulated 4H-Pyrans Based on a Cu(I)-Catalyzed C-Allylation/O-Vinylation Reaction of Cyclic 1-Bromoallyl Tosylates with Cyclic and Acyclic 1,3-Dicarbonyls J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Mehran Khoshbakhsh Foumani, Jürgen Conrad, Wolfgang Frey, Uwe Beifuss
The Cu(I)-catalyzed reaction between five-, six-, seven-, and eight-membered cyclic 1-bromoallyl tosylates and five- and six-membered cyclic 1,3-dicarbonyls in DMF at 80 °C using Cs2CO3 as a base and 2-picolinic acid as an additive selectively delivers a wide array of bisannulated 4H-pyrans in a single step with yields up to 92%. The transformations are considered to proceed as intermolecular C-al
-
Cobalt-Catalyzed Formation of Grignard Reagents via C–O or C–S Bond Activation J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Ewa Pietrasiak, Seongmin Ha, Seungwon Jeon, Jongheon Jeong, Jiyeon Lee, Jongcheol Seo, Eunsung Lee
C(aryl)–OMe bond functionalization catalyzed by cobalt(II) chloride in combination with a nacnac-type ligand and magnesium as a reductant is reported. Borylation and benzoylation of aryl methoxides are demonstrated, and C(aryl)–SMe bond borylation can be achieved under similar conditions. This is the first example of achieving these transformations using cobalt catalysis. Mechanistic studies suggest
-
Arylselenyl Radical-Mediated Cyclization of N-(2-Alkynyl)anilines: Access to 3-Selenylquinolines J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Changlei Zhu, Max Nurko, Cynthia S. Day, John C. Lukesh, III
An efficient and novel approach to accessing 3-selenylquinolines from diaryl diselenides and acyclic, selenium-free substrates is described. Preliminary mechanistic studies indicate that the combination of CuCl2 and air affords an appropriate environment for producing arylselenyl radicals that initiate the cascade cyclization of N-(2-alkynyl)anilines, forming key Se–C and C–C bonds in a single step
-
Nickel-Catalyzed Tandem Ueno–Stork Cyclization: Stereoselective 1,2-Dicarbofunctionalization of Cyclic Alkenes J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Pedro de Andrade Horn, Hunter S. Sims, Mingji Dai
A nickel-catalyzed tandem Ueno–Stork cyclization is developed to enable stereoselective 1,2-dicarbofunctionalization of cyclic alkenes and efficiently build various bicyclic products. This new protocol does not involve any toxic or difficult-to-remove tin reagent and is scalable and amenable to build all-carbon quaternary centers.
-
Selective C3-Allylation and Formal [3 + 2]-Annulation of Spiro-Aziridine Oxindoles: Synthesis of 5′-Substituted Spiro[pyrrolidine-3,3′-oxindoles] and Coerulescine J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 SK Abu Saleh, Atanu Hazra, Maya Shankar Singh, Saumen Hajra
Brønsted acid- and/or Lewis acid-catalyzed selective C3-allylation and formal [3 + 2]-annulation of spiro-aziridine oxindoles with allylsilanes have been demonstrated to deliver direct access to 3-allyl-3-aminomethyl oxindoles and 5-silyl methyl spiro[pyrrolidine-3,3′-oxindoles], respectively. The acid-catalyzed methods do not provide any stereoselectivity when chiral spiroaziridines are used. However
-
One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Ilya P. Filippov, Mikhail S. Novikov, Alexander F. Khlebnikov, Nikolai V. Rostovskii
A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared
-
Synthesis of β2,2-Amino Acids by Stereoselective Alkylation of Isoserine Derivatives Followed by Nucleophilic Ring Opening of Quaternary Sulfamidates J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Pablo Tovillas, Claudio D. Navo, Paula Oroz, Alberto Avenoza, Francisco Corzana, María M. Zurbano, Gonzalo Jiménez-Osés, Jesús H. Busto, Jesús M. Peregrina
Chiral bicyclic N,O-acetal isoserine derivatives have been synthesized by an acid-catalyzed tandem N,O-acetalization/intramolecular transcarbamoylation reaction between conveniently protected l-isoserine and 2,2,3,3-tetramethoxybutane. The delicate balance of the steric interactions between the different functional groups on each possible diastereoisomer controls their thermodynamic stability and hence
-
Stereoselective Access to Iminosugar C,C-Glycosides from 6-Azidoketopyranoses Org. Lett. (IF 6.005) Pub Date : 2022-06-22 Zakaria Debbah, Jérôme Marrot, Nicolas Auberger, Jérôme Désiré, Yves Blériot
We report the synthesis of iminosugar C,C-glycosides starting from 6-azidoketopyranoses. Their Staudinger-azaWittig-mediated cyclization provided bicyclic N,O-acetals, which were stereoselectively opened with AllMgBr to afford β-hydroxyazepanes with a quaternary carbon α to the nitrogen. Their ring contraction via a β-aminoalcohol rearrangement produced the six-membered l-iminosugars with two functional
-
Palladium-Catalyzed Regioselective [5 + 1] Annulation of Vinyl Aziridines/Epoxides with ClCF2COONa Org. Lett. (IF 6.005) Pub Date : 2022-06-22 Dandan Zuo, Tao Zhang, Jingjing Zhao, Wen Luo, Chaojie Wang, Pan Li
Palladium-catalyzed regioselective [5 + 1] annulation reactions of vinyl aziridines/epoxides with ClCF2COONa have been developed. Significantly, vinyl aziridines/epoxides act as heteroatom-containing five-atom synthons, and commercially available and cheap ClCF2COONa acts as the source of carbonyl serving as a difluorocarbene precursor. This protocol provides an efficient and practical method for the
-
Synthesis of Nitrogen-Doped Aza-Helicenes with Chiral Optical Properties J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Xue Gong, Chunmei Li, Zhixiong Cai, Xuejuan Wan, Haixia Qian, Guanghui Yang
Aza-helicenes are one of the most important series of heterohelicenes; herein, a series of novel aza-helicenes (5H, 6H, 6S, and 8S) were prepared via Bischler–Napieralski cyclization, and the interconversion dynamic process of these aza-helicenes was revealed using density functional theory calculations. The novel nitrogen-doped [6]helicene (6H) possesses a very high interconversion energy barrier
-
Solvent-Free Mechanosynthesis of Polysubstituted 1,2-Dihydroquinolines from Anilines and Alkyne Esters J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Hui Xu, Guan-Wu Wang
A novel one-pot reaction of anilines with acetylenedicarboxylate diesters in the presence of boron trifluoride, iodine, and trifluoroacetic acid or methylsulfonic acid has been developed under solvent-free ball-milling conditions, affording a variety of polysubstituted 1,2-dihydroquinolines bearing multiple ester groups in moderate to excellent yields. The present protocol features mild reaction conditions
-
Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Yuan Zhang, Tongda Liu, Li Liu, Haiyang Guo, Heyang Zeng, Wei Bi, Guanyinsheng Qiu, Wei Gao, Xin Ran, Long Yang, Guanben Du, Lianpeng Zhang
Here, we report a novel and facile protocol for the synthesis of benz[c,d]indol-2-imines via palladium-catalyzed C–C and C–N coupling of 8-halo-1-naphthylamines with isocyanides in a single step. The reaction features broad substrate scopes and mild conditions, providing an efficient alternative for the construction of antiproliferative agents and BET bromodomain inhibitors. If 0.1 mL of H2O was added
-
Visible-Light-Induced Oxyalkylation of 1,2,4-Triazine-3,5(2H, 4H)-diones with Ethers via Oxidative Cross-Dehydrogenative Coupling J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Yushi Tan, Wu Xuekun, Ya-Ping Han, Yuecheng Zhang, Hong-Yu Zhang, Jiquan Zhao
An efficient and convenient method to synthesize 6-oxyalkylated 1,2,4-triazine-3,5(2H, 4H)-diones has been developed via visible-light-induced cross-dehydrogenative coupling reaction between 1,2,4-triazine-3,5(2H, 4H)-diones and ethers with a wide range of functional group tolerance. The present transformation employs the cheap and low-toxic 2-tert-butylanthraquinone as a metal-free photocatalyst and
-
Fe-Catalyzed Three-Component Coupling Reaction of α,β,γ,δ-Unsaturated Carbonyl Compounds and Conjugate Dienes with Alkylsilyl Peroxides and Nucleophiles J. Org. Chem. (IF 4.354) Pub Date : 2022-06-22 Hanbin Lu, Canhua Zhou, Zhe Wang, Terumasa Kato, Yan Liu, Keiji Maruoka
An Fe(OTf)2-catalyzed three-component coupling reaction of α,β,γ,δ-unsaturated carbonyl compounds with alkylsilyl peroxides in the presence of certain heteronucleophiles (ROH and indole) is realized under mild reaction conditions. A variety of α,β,γ,δ-diene carbonyl substrates with different substituents were successfully employable via combination with several different alkylsilyl peroxides. This
-
Synthesis, Characterization, and Properties of BN-Fluoranthenes Org. Lett. (IF 6.005) Pub Date : 2022-06-22 Erlong Li, Mengjia Jin, Ruijun Jiang, Lei Zhang, Yanli Zhang, Meiyan Liu, Xiaoming Wu, Xuguang Liu
Boron/nitrogen-doped fluoranthenes, a new class of BN-doped cyclopenta-fused polycyclic aromatic hydrocarbons, were synthesized via pyrrolic-type nitrogen directed C–H borylation. Regioselective bromination of BN-fluoranthene (3a) gave mono- and dibrominated BN-fluoranthenes. The halogenated BN-fluoranthene (3b) can undergo various of further cross-coupling reactions to deliver a series of BN-fluoranthenes
-
Attached Nitrogen Test by 13C–14N Solid-State NMR Spectroscopy for the Structure Determination of Heterocyclic Isomers Org. Lett. (IF 6.005) Pub Date : 2022-06-22 Rick W. Dorn, Brendan J. Wall, Sarah B. Ference, Sean R. Norris, Joseph W. Lubach, Aaron J. Rossini, Brett VanVeller
Differentiation of heterocyclic isomers by solution 1H, 13C, and 15N NMR spectroscopy is often challenging due to similarities in their spectroscopic signatures. Here, 13C{14N} solid-state NMR spectroscopy experiments are shown to operate as an “attached nitrogen test”, where heterocyclic isomers are easy to distinguish based on one-dimensional nitrogen-filtered 13C solid-state NMR. We anticipate that
-
Synthesis and Spectral Properties of Aggregation-Induced Emission-Active Push–Pull Chromophores Based On Isoindole Scaffolds Org. Lett. (IF 6.005) Pub Date : 2022-06-22 Changjiang Yu, Xingbao Fang, Qinghua Wu, Xing Guo, Na Chen, Chao Cheng, Erhong Hao, Lijuan Jiao
A new class of tailor-made push–pull isoindole fluorophores has been synthesized through the combination of Suzuki coupling and Knoevenagel reactions. The efficient synthetic strategy rendered the isoindole scaffold as the π-bridge and the isolation spacer and provided dyes bearing various types of electron donors and electron acceptors for manipulating their energy gaps and tuning their absorptions