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Cp*RhIII-Catalyzed Cascade Annulation of Arylimidates with Pyridotriazoles toward Isoquinolin-3-ol Derivatives J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Weidan Yan, Hong Luo, Qiling Wu, Liansheng Liu, Jing Li, Junfa Wei
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Re-Evaluation of Product Outcomes in the Rh-Catalyzed Ring Expansion of Aziridines with N-Sulfonyl-1,2,3-Triazoles J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Hillary J. Dequina, Josephine Eshon, Steven C. Schmid, William T. Raskopf, Kyana M. Sanders, Israel Fernández, Jennifer M. Schomaker
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Palladium-Catalyzed Intramolecular Heck Dearomative Alkenylation of Indoles with N-Tosylhydrazones J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Shao-Bo Duan, Hong-Yu Zhang, Yue Ma, Jiquan Zhao, Ya-Ping Han, Yuecheng Zhang, Yong-Min Liang
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Total Synthesis of Marine Alkaloids Cystodytins A–K J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Dongfang Jiang, Yang Chen, Shaozhong Wang
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Stereocontrolled Synthesis of C20S-C26 and C20R-C26 Fragments of Amphidinolide L J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Jun Koizumi, Kaoru Tanaka, Keisuke Fukaya, Daisuke Urabe
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Total Synthesis of Isohericerinol A and Its Analogues to Access Their Potential Neurotrophic Effects J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Manjunatha Vishwanath, Chhabi Lal Chaudhary, Yunjeong Park, Mayavan Viji, Chanhyun Jung, Kwanghee Lee, Jaeuk Sim, Seong Min Hong, Da Hye Yoon, Dae Hee Lee, Jae Kang Lee, Heesoon Lee, Mi Kyeong Lee, Sun Yeou Kim, Jae-Kyung Jung
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Structures and Oxidation Properties of Phenylene-Bridged Diazacycloalkanes: Ring Size Effects on Structures and Properties J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Wataru Setaka, Kazuki Kajiyama, Yusuke Inagaki
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Rhodium(III)-Catalyzed Redox-Neutral [4 + 1]-Annulation of Unactivated Alkenes with Sulfoxonium Ylides J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Pinki Sihag, Masilamani Jeganmohan
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Determination of the Rate Constant of the [4 + 2] Cycloaddition Between an Aryne Atropisomer and Furan in Solution J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Guillaume Dauvergne, Nicolas Vanthuyne, Michel Giorgi, Jean Rodriguez, Yannick Carissan, Yoann Coquerel
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Dual Photoredox Ni/Benzophenone Catalysis: A Study of the NiII Precatalyst Photoreduction Step J. Org. Chem. (IF 4.198) Pub Date : 2022-08-10 Axel Almansa, Damien Jardel, Stéphane Massip, Thierry Tassaing, Christophe Schatz, Jérémy Domergue, Florian Molton, Carole Duboc, Jean-Marc Vincent
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Gold-Catalyzed 1,3-Thiazine Formation and Uncommon Tautomer Isolation J. Org. Chem. (IF 4.198) Pub Date : 2022-08-09 Guillermo Canudo-Barreras, Daniel Salvador, Raquel P. Herrera, M. Concepción Gimeno
This work represents the first example of a gold-catalyzed formation of 1,3-thiazine/1,3-thiazinane by means of a catalytic approach and further uncommon isolation of the two tautomers. The developed protocol gives rise to a broad scope of 1,3-thiazine derivatives with excellent yields in short reaction times. Interestingly, different isomers could be obtained depending on the state of the compound
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Electrophilic Reagents for the Direct Incorporation of Uncommon SCF2CF2H and SCF2CF3 Motifs J. Org. Chem. (IF 4.198) Pub Date : 2022-08-09 Jordi Mestre, Miguel Bernús, Sergio Castillón, Omar Boutureira
The introduction of fluoroalkylthioether groups has attracted the attention of the drug-discovery community given the special physicochemical and pharmacokinetic features they confer to bioactive compounds, yet these are often limited to standard SCF3 and SCF2H moieties. Herein, two saccharin-based electrophilic reagents have been disclosed for the incorporation of uncommon SCF2CF2H and SCF2CF3 motifs
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Selective C–F Bond Etherification of Trifluoromethylalkenes with Phenols J. Org. Chem. (IF 4.198) Pub Date : 2022-08-09 Qingqiang Tian, Boqun Pei, Chuxia Wang, Chiying Zhang, Yahui Li
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Intramolecular Diels–Alder Reactions of α-Bromostyrene-Functionalized Unsaturated Carboxamides J. Org. Chem. (IF 4.198) Pub Date : 2022-08-09 Zhichao Wang, Shoko Yamazaki, Yuji Mikata, Miho Oba, Hiroshi Takashima, Tsumoru Morimoto, Akiya Ogawa
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Vacatadithiasapphyrins: Synthesis, Structure, and Spectral and Redox Properties J. Org. Chem. (IF 4.198) Pub Date : 2022-08-09 Md Ashif Ali, Mangalampalli Ravikanth
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Synthesis of β-Arylseleno Sulfoximines: A Metal-Free Three-Component Reaction Mediated by Tetrabutylammonium Tribromide J. Org. Chem. (IF 4.198) Pub Date : 2022-08-08 Xiaoman Li, Jiawei Huang, Liang Xu, Ping Liu, Yu Wei
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Visible-Light-Induced Photocatalytic Trifluoromethylation of Bunte Salts: Easy Access to Trifluoromethylthiolated Synthons J. Org. Chem. (IF 4.198) Pub Date : 2022-08-08 Neha Sharma Prabhakar, Saurabh Kumar, Prince Kumar Gupta, Krishna Nand Singh
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Controlling the Enantioselectivity in an Adaptable Ligand by Biomimetic Intramolecular Interlocking J. Org. Chem. (IF 4.198) Pub Date : 2022-08-08 Jan-Michael Menke, Oliver Trapp
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Chiral Assemblies of Planar and Achiral meta-Arylene Ethynylene Macrocycles Induced by Saccharide Recognition J. Org. Chem. (IF 4.198) Pub Date : 2022-08-08 Yuki Ohishi, Junya Chiba, Masahiko Inouye
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Rh(III)-Catalyzed Tandem Reaction Access to (Quinazolin-2-yl)methanone Derivatives from 2,1-Benzisoxazoles and α-Azido Ketones J. Org. Chem. (IF 4.198) Pub Date : 2022-08-08 Shan Liu, An-Jing Wang, Min Li, Jing Zhang, Guo-Dong Yin, Wen-Ming Shu, Wei-Chu Yu
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A Practical Method for the Large-Scale Preparation of the P-Chiral Dihydrobenzoazaphosphole Core by Chemical Resolution J. Org. Chem. (IF 4.198) Pub Date : 2022-08-05 Jean-Nicolas Desrosiers, Yibo Xu, Stephanie C. Kosnik, Bo Qu, Kendricks S. Lao, Chris H. Senanayake, Yongda Zhang
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Ru(II)-Catalyzed Regioselective C(5)–H Functionalization of Quinazolinone-Coumarin Conjugates: Synthesis and Photophysical Studies J. Org. Chem. (IF 4.198) Pub Date : 2022-08-05 Dinesh Singla, Kamaldeep Paul
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Direct Benzylic C(sp3)–O Coupling with Alcohol via Site-Selective C(sp3)–H Cleavage at Room Temperature through a Remote Directing Group-Enabled Radical Relay Strategy J. Org. Chem. (IF 4.198) Pub Date : 2022-08-05 Fang Wang, Jiaming Chen, Xiaoqi Jia, Dailin Zhuang, Zhenyang Wan, Lifang Ma, Ziyuan Li
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Stereo- and Regioselectivity of Hydrogenation of a Recently Synthesized Carboncone and Its Predictive Models J. Org. Chem. (IF 4.198) Pub Date : 2022-08-05 Xuyang Chen, Yuanyuan Sun, Yang Wang
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Silyl Cation-Initiated, Brønsted Acid-Catalyzed Strategy toward Unsymmetrical 3,3-Disubstituted 2-Oxindoles and Azonazine Cores J. Org. Chem. (IF 4.198) Pub Date : 2022-08-05 Jabir Khan, Naveen Yadav, Aparna Tyagi, Chinmoy Kumar Hazra
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Visible-Light-Induced α-C(sp3)–H Phosphinylation of Unactivated Ethers under Photocatalyst- and Additive-Free Conditions J. Org. Chem. (IF 4.198) Pub Date : 2022-08-05 Bo Liu, Jianji Li, Yifan Hu, Qian Chen, Yan Liu, Shaomin Ji, Keiji Maruoka, Yanping Huo, Hao-Li Zhang
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Thiol Reactivity of N-Aryl α-Methylene-γ-lactams: Influence of the Guaianolide Structure J. Org. Chem. (IF 4.198) Pub Date : 2022-08-05 Daniel P. Dempe, Chong-Lei Ji, Peng Liu, Kay M. Brummond
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Gram-Scale Asymmetric Synthesis of Fluorinated Amino Acids Using a Chiral Nickel(II) Complex J. Org. Chem. (IF 4.198) Pub Date : 2022-08-04 Thomas Hohmann, Michael Dyrks, Suvrat Chowdhary, Manuela Weber, Duy Nguyen, Johann Moschner, Beate Koksch
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Chemoselective Oxidation of Thiols with Oxoammonium Cations J. Org. Chem. (IF 4.198) Pub Date : 2022-08-04 Shayne M. Weierbach, Robert P. Reynolds, Shannon M. Stephens, Kostantinos V. Vlasakakis, Ramsey T. Ritter, Olivia M. White, Nishi H. Patel, Eric C. Hayes, Sydney Dunmire, Kyle M. Lambert
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Pd-Catalyzed Alkyne and Aryne Annulations: Synthesis and Photophysical Properties of π-Extended Coumarins J. Org. Chem. (IF 4.198) Pub Date : 2022-08-04 Hemanta Hazarika, Dhiraj Dutta, Sanfaori Brahma, Babulal Das, Pranjal Gogoi
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Visible Light Photoredox-Catalyzed Direct C–H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts J. Org. Chem. (IF 4.198) Pub Date : 2022-08-04 Raj K. Samanta, Prahallad Meher, Sandip Murarka
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Solvent Dependent Competitive Mechanisms for the Ugi Multicomponent Reaction: A Joint Theoretical and Experimental Study in the α-Acyl Aminocarboxamides vs α-Amino Amidines Formation J. Org. Chem. (IF 4.198) Pub Date : 2022-08-04 Marcelo H. R. Carvalho, João P. R. S. Ribeiro, Pedro P. De Castro, Saulo T. A. Passos, Brenno A. D. Neto, Hélio F. Dos Santos, Giovanni W. Amarante
A synthetic protocol for the preparation of α-acyl aminocarboxamides and α-amino amidines is proposed. The selectivity toward each of these two possible products was tuned by simple modifications of the reaction conditions. A broad scope is presented, allowing access to the desired products in up to 87% (Ugi adduct) and 93% (α-amino amidine). Theoretical calculations were carried out, and the analysis
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Electrochemical Cyclization of Alkynyl Enaminones: Controllable Synthesis of Indeno[1,2-c]pyrroles or Indanones J. Org. Chem. (IF 4.198) Pub Date : 2022-08-04 Yulei Zhao, Yuhang Fan, Xiaohan Meng, Xin Kang, Zhongyin Ji, Shina Yan, Laijin Tian
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Bicyclization of 4-Cyano-1,2-diketones with Amidines: Synthesis of Tetrahydroimidazo[4,5-b]-5-pyridinones J. Org. Chem. (IF 4.198) Pub Date : 2022-08-04 Xiaowei Liu, Chi Gao, Mang Wang
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Heck Reaction of 2-Oxyacrylates with Aryl Bromides: A Common Route to Monoaryl Pyruvates and Ortho Ester-Protected Monoaryl Pyruvates J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Kiran Matcha, Konstantin Chernichenko, Kévin Jouvin, Suresh Babu Guduguntla, Duc N. Tran, Stephen Bell, Warren Paden, Marek Figlus, Colin Muir, Alain Elliott, Cristina Hernandez Diaz
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Synthesis of 2-Deoxyglycosides Bearing Free Hydroxyl Substituents on the Glycosyl Donor J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Kevin M. Hoang, Xiaoying Zheng, Seth B. Herzon
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Cu(OTf)2/NBS-Mediated Tandem Reaction of 1-Cinnamyl Alcohol-o-Carboranes via Ring Opening of Oxetane with Arenes: An Alternative Approach for the Synthesis of C-Alkenyl-o-Carboranes J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Cai-Yan Zhang, Ke Cao, Han-Bo Yang, Li-Fang Ding, Junxiao Yang
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Construction of 3,12-Diazatetracyclododecane-dienes through Unexpected Visible-Light-Induced Radical Cascade Cyclization J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Qidi Zhong, Yinxin Wang, Hanyang Lan, Hao Zhu, Qiangwen Fan
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Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Rubén M. Carballo, José M. Padrón, Israel Fernández, Daniel A. Cruz, Luana Grmuša, Víctor S. Martín, Juan I. Padrón
A direct, catalytic, and complementary method to obtain 2-substituted homoallyl sulfonyl amides is described, starting from sulfonyl amides, aldehydes, and allyltrimethylsilane using iron(III) chloride as a sustainable catalyst. The scope of the process and the reactivity in aza-Prins cyclization is evaluated and supported by density functional theory (DFT) studies. Finally, an evaluation of the antiproliferative
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Concise Synthesis of Spirocyclic Dihydrophthalazines through Spiroannulation Reactions of Aryl Azomethine Imines with Cyclic Diazo Compounds J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Xinyuan Cai, Xia Song, Qiuhui Zhu, Xinying Zhang, Xuesen Fan
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Total Synthesis of Leptochartamides A and B: Two Enantiomeric Pairs of Hydroxybenzyl Dimers from a Deep-Sea Fungus Leptosphaerulina chartarum J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Meimei Cheng, Xuechao Cui, Yu Tang, Zongze Shao, Xiupian Liu, Juncheng Su, Jian Zhang, Qi Wang, Guoqiang Li
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Reversible, Red-Shifted Photoisomerization in Protonated Azobenzenes J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Jonas Rickhoff, Niklas B. Arndt, Marcus Böckmann, Nikos L. Doltsinis, Bart Jan Ravoo, Luuk Kortekaas
Azobenzenes are among the best-studied molecular photoswitches and play a key role in the search for red-shifted photoresponsive materials for extended applications. Currently, most approaches deal with aromatic substitution patterns to achieve visible light application, on occasion paired with protonation to yield red-shifted absorption of the azonium species. Appropriate substitution patterns are
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Direct Assembly of Diverse Unsymmetrical Tertiary 9-Fluorenols via Transient Directing Group-Enabled Palladium-Catalyzed Dual C–H Bond Activation of α-Ketoesters J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Wengang Xu, Yangyang Zhang, Yongdi Wu, Jian Wang, Xuelian Lu, Yirong Zhou, Fang-Lin Zhang
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Diversification of (E,E)-1,6-Dioxo-2,4-Dienes for the Synthesis of (+)-Aspicillin, Isolaurepan, and β-Parinaric Acid J. Org. Chem. (IF 4.198) Pub Date : 2022-08-03 Dattatraya H. Dethe, Aparna Srivastava, Appasaheb K. Nirpal, Nagabhushana C. Beeralingappa, Vimlesh Kumar, Arsheed A. Bhat
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MgI2-Catalyzed Nucleophilic Ring-Opening Reactions of Donor–Acceptor Cyclopropanes with Indoline-2-thiones J. Org. Chem. (IF 4.198) Pub Date : 2022-08-02 Pan Tang, You-Yuan Wei, Long Wen, Hao-Jie Ma, Yi Yang, Yan Jiang
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Insight into Substrate Recognition by Urea-Based Helical Foldamer Catalysts Using a DFT Global Optimization Approach J. Org. Chem. (IF 4.198) Pub Date : 2022-08-02 Yaidel Toledo-González, Jean-Marc Sotiropoulos, Diane Bécart, Gilles Guichard, Philippe Carbonnière
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One-Pot Reductive Methylation of Nitro- and Amino-Substituted (Hetero)Aromatics with DMSO/HCOOH: Concise Synthesis of Fluorescent Dimethylamino-Functionalized Bibenzothiazole Ligands with Tunable Emission Color upon Complexation J. Org. Chem. (IF 4.198) Pub Date : 2022-08-02 Patrik Osuský, Maroš Smolíček, Jela Nociarová, Erik Rakovský, Peter Hrobárik
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[Pt(PPh3)4]-Catalyzed Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes J. Org. Chem. (IF 4.198) Pub Date : 2022-08-02 Jakub Szyling, Aleksandra Szymańska, Adrian Franczyk, Jędrzej Walkowiak
A straightforward, efficient, and selective method for the preparation of novel boryl-functionalized enynes or dienes via [Pt(PPh3)4]-catalyzed diboration of a broad spectrum of symmetrical and unsymmetrical 1,3-diynes was developed. The catalytic cycle of diboration was proposed on the basis of low-temperature 31P NMR studies. An alternative isolation method via product condensation on a cold finger
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Electrochemical Aerobic Oxygenation and Nitrogenation of Cyclic Alkenes via C═C Bond Cleavage or Oxygenation and Azidation of Open-Chain Alkenes J. Org. Chem. (IF 4.198) Pub Date : 2022-08-02 Yan Zhu, Cong Jiang, Heng Li, Ping Liu, Peipei Sun
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Olefination of 3-Diazoindolin-2-imines with Hydrazones: An Approach toward Stereoselective Synthesis of (E)-3-Arylideneindolin-2-imines J. Org. Chem. (IF 4.198) Pub Date : 2022-08-02 Jianwei Xie, Li Wu, Ping Lu, Yanguang Wang
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TBAI-Catalyzed S–H and N–H Insertion Reactions of α-Diazoesters with Thiophenols and Amines under Metal-Free Conditions J. Org. Chem. (IF 4.198) Pub Date : 2022-08-02 Rongxiang Chen, Guoyang Ma, Yawen Li, Jinju Zhang, Ran Xia, Kai-Kai Wang, Lantao Liu
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Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones J. Org. Chem. (IF 4.198) Pub Date : 2022-08-01 Suvajit Koley, Kaylee T. Cayton, Gisela A. González-Montiel, M. Ramu Yadav, Douglas L. Orsi, Andrew J. Intelli, Paul Ha-Yeon Cheong, Ryan A. Altman
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Bioinspired Iron-Catalyzed Dehydration of Aldoximes to Nitriles: A General N–O Redox-Cleavage Method J. Org. Chem. (IF 4.198) Pub Date : 2022-08-01 Hongjie Gao, Jia-Yi Chen, Zhiqiang Peng, Lei Feng, Chen-Ho Tung, Wenguang Wang
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FeCl3-Catalyzed Synthesis of Tanshinlactone Analogues from 1H-Indene-1,2,3-triones and Alkynes J. Org. Chem. (IF 4.198) Pub Date : 2022-08-01 Zhenzhu Hu, Peng Ma, Ning Ma, Jianhui Wang
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Photocatalytic Hydroalkylation of Aryl-Alkenes J. Org. Chem. (IF 4.198) Pub Date : 2022-08-01 Cornelia S. Buettner, Michael Schnürch, Katharina Bica-Schröder
Here, we present a visible light-catalyzed hydroalkylation of aryl-alkenes affording C–C bonds using aryl-alkenes and alkyl iodides. We demonstrate the formation of various hydroalkylation products in excellent yields, with primary, secondary, and tertiary alkyl iodides being tolerated in the reaction. Mechanistic experiments reveal a pathway consisting of halogen atom transfer followed by a radical-polar
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Synthesis of Isoxazoles via One-Pot Oxidation/Cyclization Sequence from Propargylamines J. Org. Chem. (IF 4.198) Pub Date : 2022-07-31 Mengyan Duan, Guodong Hou, Yabiao Zhao, Congjun Zhu, Chuanjun Song
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Visible Light-Mediated Enantioselective Addition of α-Aminoalkyl Radicals to Ketones Catalyzed by Chiral Oxazaborolidinium Ion J. Org. Chem. (IF 4.198) Pub Date : 2022-07-30 Soo Min Cho, Jae Yeon Kim, Shinyeong Han, Do Hyun Ryu
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Revisiting the Mg/TMSCl/Dipolar Solvent System for Dearomatic Silylation of Aryl Carbonyl Compounds: Substrate Scope, Transformations, and Mechanistic Studies J. Org. Chem. (IF 4.198) Pub Date : 2022-07-29 Nan-Nan Li, Meng Li, Jia-Ni Gao, Zhong Zhang, Jian-Bo Xie
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Two-Step Construction of Thiophene–Oxazole Dyads with Fluorescent Properties by the Ring Expansion of Aziridines J. Org. Chem. (IF 4.198) Pub Date : 2022-07-29 Alena S. Pankova
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Why [4 + 2 + 1] but Not [2 + 2 + 1]? Why Allenes? A Mechanistic Study of the Rhodium-Catalyzed [4 + 2 + 1] Cycloaddition of In Situ Generated Ene–Ene–Allenes and Carbon Monoxide J. Org. Chem. (IF 4.198) Pub Date : 2022-07-29 Yusheng Yang, Zi-You Tian, Chen-Long Li, Zhi-Xiang Yu