15 Apr 19:21
Chem. Soc. Rev., 2022, 51,2313-2382
DOI: 10.1039/D1CS00510C, Review Article
Guglielmo A. Coppola, Serena Pillitteri, Erik V. Van der Eycken, Shu-Li You, Upendra K. Sharma
This review offers an overview of recent synthetic strategies employing photoredox catalysis and electrochemistry in the framework of multicomponent reactions.
The content of this RSS Feed (c) The Royal Society of Chemistry
15 Apr 12:23
Org. Biomol. Chem., 2022, 20,2896-2908
DOI: 10.1039/D2OB00101B, Paper
Niklas Lohmann, Vesna Milovanović, Dariusz G. Piekarski, Olga García Mancheño
A one-pot, oxidative Ugi-azide multicomponent reaction mediated by oxoammonium salts is presented. This method provides a direct access to α-tetrazolo N-heterocycles in excellent yields employing simple NaN3 as azide source.
The content of this RSS Feed (c) The Royal Society of Chemistry
15 Apr 11:48
Chem. Commun., 2022, 58,4771-4774
DOI: 10.1039/D2CC00807F, Communication
Rui Shao, Haixia Zhao, Shumin Ding, Lianjie Li, Chen Chen, Jian Wang, Yongjia Shang
We herein reported the first silver-promoted [3+4] cycloaddition of α-isocyanoacetates with anthranils as aromatic Michael accepters. Benzo[d][1,3]diazepinones were accessed under mild conditions through an “oxygen migration” rearrangement process.
The content of this RSS Feed (c) The Royal Society of Chemistry
14 Apr 08:24
by Jacqueline Bitai,
Alastair J. Nimmo,
Alexandra M. Z. Slawin,
Andrew David Smith
Cooperative palladium and isothiourea catalysis allows the formal (3+2) cycloaddition of vinylcyclopropanes and α,β-unsaturated esters to generate functionalized cyclopentanes via an α,β-unsaturated acyl ammonium intermediate with the addition of LiCl crucial to obtain high product diastereo- and enantioselectivity.
Abstract
A protocol for the enantioselective synthesis of substituted vinylcyclopentanes has been realised using cooperative palladium and isothiourea catalysis. Treatment of vinylcyclopropanes with Pd(PPh3)4 generates a zwitterionic π-allyl palladium intermediate that intercepts a catalytically generated α,β-unsaturated acyl ammonium species prepared from the corresponding α,β-unsaturated para-nitrophenyl ester and the isothiourea (R)-BTM. Intermolecular formal (3+2) cycloaddition between these reactive intermediates generates functionalised cyclopentanes in generally good yields and excellent diastereo- and enantiocontrol (up to >95 : 5 dr, 97 : 3 er), with the use of LiCl as an additive proving essential for optimal stereocontrol. To the best of our knowledge a dual transition metal/organocatalytic process involving α,β-unsaturated acyl ammonium intermediates has not been demonstrated previously.
14 Apr 08:18
by Feng-Lian Zhang, Bin Li, K. N. Houk, and Yi-Feng Wang
JACS Au
DOI: 10.1021/jacsau.2c00051
30 Mar 14:19
by Rose M. McLellan, Rosannah C. Cameron, Matthew J. Nicholson, and Emily J. Parker
Organic Letters
DOI: 10.1021/acs.orglett.2c00473
28 Feb 16:30
Chem. Commun., 2022, 58,3847-3864
DOI: 10.1039/D2CC00369D, Highlight
Yanan Wang, Yanyang Bao, Meifang Tang, Zhegao Ye, Zheliang Yuan, Gangguo Zhu
This review summarises recent applications of pyridinium salts in radical-mediated difunctionalization of alkenes. We hope this review will provide a comprehensive overview of this topic and promote the wider development and application of pyridinium salts.
The content of this RSS Feed (c) The Royal Society of Chemistry
16 Feb 13:58
by Mina Yamane, Yamato Kanzaki, Harunobu Mitsunuma, and Motomu Kanai
Organic Letters
DOI: 10.1021/acs.orglett.2c00138
27 Jan 08:47
by Kengo Hyodo, Kensho Miki, and Tomoya Yauchi
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.1c02809
27 Jan 08:45
by Wenxuan Zhang, Ran Song, Daoshan Yang, and Jian Lv
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.1c02750
18 Jan 17:03
by Xu Cheng, Aiwen Lei, Tian-Sheng Mei, Hai-Chao Xu, Kun Xu & Chengchu Zeng1School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 2100232College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University, Wuhan 4300723State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 2000324State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 3610055Faculty of Environment and Life, Beijing University of Technology, Beijing 100124
CCS Chemistry, <a href="https://www.chinesechemsoc.org/toc/ccschem/4/4">Volume 4, Issue 4</a>, Page 1120-1152, April 2022.
04 Jan 10:07
Chem. Sci., 2022, 13,1088-1094
DOI: 10.1039/D1SC06613G, Edge Article
Open Access
Hui Liang, Dong-Sheng Ji, Guo-Qiang Xu, Yong-Chun Luo, Haixue Zheng, Peng-Fei Xu
We have developed a metal-free, visible-light driven chiral phosphoric acid catalyzed asymmetric intermolecular, three-component radical-initiated dicarbofunctionalization and oxytrifluoromethylation of enamines.
The content of this RSS Feed (c) The Royal Society of Chemistry
MRV and -1 others like this
02 Jan 22:02
by Alexander L. Guzman and Thomas R. Hoye
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.1c02590
30 Dec 17:07
by Nicholas P. Taylor, Jorge A. Gonzalez, Gary S. Nichol, Andrés García-Domínguez, Andrew G. Leach, and Guy C. Lloyd-Jones
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.1c02729
30 Dec 16:41
Chem. Commun., 2022, 58,730-746
DOI: 10.1039/D1CC05730H, Highlight
Pin Gao, Yue-Jie Niu, Fan Yang, Li-Na Guo, Xin-Hua Duan
This article provides a comprehensive perspective on three-component 1,2-dicarbofunctionalization of alkenes involving alkyl radicals, which generated from structurally diverse electrophilic and nucleophilic precursors under mild conditions.
The content of this RSS Feed (c) The Royal Society of Chemistry
30 Dec 14:54
by Aurélie Claraz and Géraldine Masson
ACS Organic & Inorganic Au
DOI: 10.1021/acsorginorgau.1c00037
20 Dec 11:05
by Salim Javed, Arghya Ganguly, Gihan C. Dissanayake, and Paul R. Hanson
Organic Letters
DOI: 10.1021/acs.orglett.1c03350
11 Dec 20:42
by Yueyue Ma, Jufei Hong, Xiantong Yao, Chengyu Liu, Ling Zhang, Youtian Fu, Maolin Sun, Ruihua Cheng, Zhong Li, and Jinxing Ye
Organic Letters
DOI: 10.1021/acs.orglett.1c03500
11 Dec 20:06
Org. Biomol. Chem., 2022, 20,362-365
DOI: 10.1039/D1OB02291A, Communication
Aline Makhloutah, Danylo Hatych, Thomas Chartier, Lou Rocard, Antoine Goujon, François-Xavier Felpin, Piétrick Hudhomme
The first Stille-type coupling is described using nitro-perylenediimide as the electrophile and various aryl and heteroaryl organostannes.
The content of this RSS Feed (c) The Royal Society of Chemistry
05 Dec 22:15
by Mrinmay Baidya,
Debabrata Maiti,
Lisa Roy,
Suman De Sarkar
A chemoselective electrooxidative heterocoupling of two different enamines is reported for the synthesis of unsymmetrically substituted NH-pyrroles. A “magic effect” of the additive trifluoroethanol is utilized to achieve the desired chemoselectivity by tuning the oxidation potentials and controlling the activation energy of the rate-determining step.
Abstract
An electrochemical method for the synthesis of unsymmetrically substituted NH-pyrroles is described. The synthetic strategy comprises a challenging heterocoupling between two structurally diverse enamines via sequential chemoselective oxidation, addition, and cyclization processes. A series of aryl- and alkyl-substituted enamines were effectively cross-coupled from an equimolar mixture to synthesize various unsymmetrical pyrrole derivatives up to 84 % yield. The desired cross-coupling was achieved by tuning the oxidation potential of the enamines by utilizing a “magic effect” of the additive trifluoroethanol (TFE). Additionally, extensive computational studies reveal the unique role of TFE in promoting the heterocoupling process by regulating the activation energies of the reaction steps through H-bonding and C−H⋅⋅⋅π interactions. Importantly, the developed electrochemical protocol was found to be equally efficient for the homocoupling of enamines to form symmetric pyrroles up to 92 % yield.
05 Dec 22:13
by Yan Huang, Jing Hou, Le-Wu Zhan, Qian Zhang, Wan-Ying Tang, and Bin-Dong Li
ACS Catalysis
DOI: 10.1021/acscatal.1c04684
05 Dec 22:12
by Philippe-Alexandre Poisson, Gaël Tran, Céline Besnard, and Clément Mazet
ACS Catalysis
DOI: 10.1021/acscatal.1c04800
05 Dec 22:06
Green Chem., 2021, Accepted Manuscript
DOI: 10.1039/D1GC03662A, Critical Review
Volker Hessel, Nam Nghiep Tran, Mahdieh Razi Asrami, Quy Don Tran, Van Duc Long Nguyen, Marc Escribà Gelonch, Jose Luis Osorio-Tejada, Steffen Linke, Kai Sundmacher
Solvents define pivotal properties for chemical processing and chemical reactions, and can be as much game-changing as catalysts are. A solvent can be the key to a good chemical process,...
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MRV and -1 others like this
05 Dec 22:03
by Yichang Liu, Biyin Shi, Zhao Liu, Renfei Gao, Cunlong Huang, Hesham Alhumade, Shengchun Wang, Xiaotian Qi, and Aiwen Lei
Journal of the American Chemical Society
DOI: 10.1021/jacs.1c09341
02 Dec 15:11
by Ephrath Solel, Marcel Ruth, and Peter R. Schreiner
Journal of the American Chemical Society
DOI: 10.1021/jacs.1c09222
30 Nov 13:25
by Matthew C. Leech, Alessia Petti, Nour Tanbouza, Andrea Mastrodonato, Iain C. A. Goodall, Thierry Ollevier, Adrian P. Dobbs, and Kevin Lam
Organic Letters
DOI: 10.1021/acs.orglett.1c03475
21 Nov 08:55
by Christian A. Malapit, Matthew B. Prater, Jaime R. Cabrera-Pardo, Min Li, Tammy D. Pham, Timothy Patrick McFadden, Skylar Blank, and Shelley D. Minteer
Chemical Reviews
DOI: 10.1021/acs.chemrev.1c00614
