Literature DB >> 23102009

Copper-promoted sulfenylation of sp2 C-H bonds.

Ly Dieu Tran1, Ilya Popov, Olafs Daugulis.   

Abstract

An auxiliary-assisted, copper catalyzed or promoted sulfenylation of benzoic acid derivative β-C-H bonds and benzylamine derivative γ-C-H bonds has been developed. The method employs disulfide reagents, copper(II) acetate, and DMSO solvent at 90-130 °C. Application of this methodology to the direct trifluoromethylsulfenylation of C-H bonds was demonstrated.

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Year:  2012        PMID： 23102009      PMCID： PMC3498454          DOI： 10.1021/ja3092278

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  55 in total

1.  Copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF3 and elemental sulfur.

Authors:  Chao Chen; Yan Xie; Lingling Chu; Ruo-Wen Wang; Xingang Zhang; Feng-Ling Qing
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

2.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

Review 3.  Alpha-fluorinated ethers, thioethers, and amines: anomerically biased species.

Authors:  Frédéric Leroux; Peter Jeschke; Manfred Schlosser
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

4.  Direct ortho cupration: a new route to regioselectively functionalized aromatics.

Authors:  Shinya Usui; Yuichi Hashimoto; James V Morey; Andrew E H Wheatley; Masanobu Uchiyama
Journal:  J Am Chem Soc       Date:  2007-11-16       Impact factor: 15.419

Review 5.  The unique role of halogen substituents in the design of modern agrochemicals.

Authors:  Peter Jeschke
Journal:  Pest Manag Sci       Date:  2010-01       Impact factor: 4.845

6.  Selective sulfoxidation of thioethers and thioaryl boranes with nitrate, promoted by a molybdenum-copper catalytic system.

Authors:  Hanit Marom; Svetlana Antonov; Yanay Popowski; Michael Gozin
Journal:  J Org Chem       Date:  2011-06-07       Impact factor: 4.354

7.  Pd-catalyzed synthesis of Ar-SCF3 compounds under mild conditions.

Authors:  Georgiy Teverovskiy; David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-20       Impact factor: 15.336

8.  Copper-catalyzed aerobic oxidative functionalization of an arene C-H bond: evidence for an aryl-copper(III) intermediate.

Authors:  Amanda E King; Lauren M Huffman; Alicia Casitas; Miquel Costas; Xavi Ribas; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

9.  Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation.

Authors:  Vladimir N Boiko
Journal:  Beilstein J Org Chem       Date:  2010-08-18       Impact factor: 2.883

10.  An aromatic Glaser-Hay reaction.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419
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  24 in total

1.  Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-24       Impact factor: 15.336

2.  Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates.

Authors:  Milad Mesgar; Olafs Daugulis
Journal:  Org Lett       Date:  2017-07-28       Impact factor: 6.005

3.  Bidentate, monoanionic auxiliary-directed functionalization of carbon-hydrogen bonds.

Authors:  Olafs Daugulis; James Roane; Ly Dieu Tran
Journal:  Acc Chem Res       Date:  2015-03-10       Impact factor: 22.384

4.  Cobalt-promoted dimerization of aminoquinoline benzamides.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Org Lett       Date:  2015-02-17       Impact factor: 6.005

5.  Pd(II)-catalyzed C-H iodination using molecular I2 as the sole oxidant.

Authors:  Xiao-Chen Wang; Yi Hu; Samuel Bonacorsi; Yang Hong; Richard Burrell; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-07-09       Impact factor: 15.419

6.  Structural reevaluation of the electrophilic hypervalent iodine reagent for trifluoromethylthiolation supported by the crystalline sponge method for X-ray analysis.

Authors:  Ekaterina V Vinogradova; Peter Müller; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

7.  Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers.

Authors:  Jian He; Caiyou Chen; Gregory C Fu; Jonas C Peters
Journal:  ACS Catal       Date:  2018-10-31       Impact factor: 13.084

8.  Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Authors:  Enrico T Nadres; Gerson Ivan Franco Santos; Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2013-09-19       Impact factor: 4.354

9.  Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

Authors:  Ly Dieu Tran; James Roane; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-24       Impact factor: 15.336

10.  Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  Tetrahedron       Date:  2015-08-19       Impact factor: 2.457
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