Literature DB >> 25100616

Exceedingly fast copper(II)-promoted ortho C-H trifluoromethylation of arenes using TMSCF₃.

Ming Shang1, Shang-Zheng Sun, Hong-Li Wang, Brian N Laforteza, Hui-Xiong Dai, Jin-Quan Yu.   

Abstract

The direct ortho-trifluoromethylation of arenes, including heteroarenes, with TMSCF3 has been accomplished by a copper(II)-promoted C-H activation reaction which completes within 30 minutes. Mechanistic investigations are consistent with the involvement of C-H activation, rather than a simple electrophilic aromatic substitution (SE Ar), as the key step.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; arenes; copper; fluorine; reaction mechanisms

Mesh：

Substances：

Year:  2014        PMID： 25100616     DOI： 10.1002/anie.201404822

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  9 in total

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Authors:  Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal:  Chem Rev       Date:  2019-01-30       Impact factor: 60.622

2.  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

Review 3.  Progress in copper-catalyzed trifluoromethylation.

Authors:  Guan-Bao Li; Chao Zhang; Chun Song; Yu-Dao Ma
Journal:  Beilstein J Org Chem       Date:  2018-01-17       Impact factor: 2.883

4.  The mechanism of directed Ni(ii)-catalyzed C-H iodination with molecular iodine.

Authors:  Brandon E Haines; Jin-Quan Yu; Djamaladdin G Musaev
Journal:  Chem Sci       Date:  2017-11-28       Impact factor: 9.825

5.  Cu(II) carboxylate arene C─H functionalization: Tuning for nonradical pathways.

Authors:  Fanji Kong; Shusen Chen; Junqi Chen; Chang Liu; Weihao Zhu; Diane A Dickie; William L Schinski; Sen Zhang; Daniel H Ess; T Brent Gunnoe
Journal:  Sci Adv       Date:  2022-08-24       Impact factor: 14.957

6.  Crystal structure of 1-methyl-3-[2,2,2-tri-fluoro-1-(1-methyl-1H-indol-3-yl)-1-phenyl-eth-yl]-1H-indole.

Authors:  Xian-Rong Liu; Yan-Ling Zhou
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-10-11

Review 7.  Collective Approach to Advancing C-H Functionalization.

Authors:  Huw M L Davies; Daniel Morton
Journal:  ACS Cent Sci       Date:  2017-09-11       Impact factor: 14.553

8.  Identification of monodentate oxazoline as a ligand for copper-promoted ortho-C-H hydroxylation and amination.

Authors:  Ming Shang; Qian Shao; Shang-Zheng Sun; Yan-Qiao Chen; Hui Xu; Hui-Xiong Dai; Jin-Quan Yu
Journal:  Chem Sci       Date:  2016-09-26       Impact factor: 9.825

9.  Catalytic activation of a single C-F bond in trifluoromethyl arenes.

Authors:  Hester Dang; Aaron M Whittaker; Gojko Lalic
Journal:  Chem Sci       Date:  2015-10-23       Impact factor: 9.825
  9 in total

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