Literature DB >> 26883690

Direct Difluoromethylation of Aryl Halides via Base Metal Catalysis at Room Temperature.

Long Xu1, David A Vicic1.   

Abstract

A stable and isolable difluoromethyl zinc reagent has been prepared through the reaction of ICF2H with diethyl zinc and DMPU. This new zinc reagent is a free-flowing solid and can be used in combination with a nickel catalyst to difluoromethylate aryl iodides, bromides, and triflates at room temperature. Such mild conditions for the catalytic difluoromethylation of these substrates are unprecedented.

Entities:  

Year:  2016        PMID： 26883690     DOI： 10.1021/jacs.6b00053

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


  15 in total

1.  Metallaphotoredox Difluoromethylation of Aryl Bromides.

Authors:  Vlad Bacauanu; Sébastien Cardinal; Motoshi Yamauchi; Masaru Kondo; David F Fernández; Richard Remy; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-28       Impact factor: 15.336

2.  Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

Authors:  Conor E Brigham; Christian A Malapit; Naish Lalloo; Melanie S Sanford
Journal:  ACS Catal       Date:  2020-07-17       Impact factor: 13.084

3.  Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

Authors:  Zhichao Lu; Olivia Hennis; Joseph Gentry; Bo Xu; Gerald B Hammond
Journal:  Org Lett       Date:  2020-05-13       Impact factor: 6.005

4.  Chlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium.

Authors:  Zhang Feng; Qiao-Qiao Min; Xia-Ping Fu; Lun An; Xingang Zhang
Journal:  Nat Chem       Date:  2017-03-14       Impact factor: 24.427

5.  Metal-free 18F-labeling of aryl-CF2H via nucleophilic radiofluorination and oxidative C-H activation.

Authors:  Gengyang Yuan; Feng Wang; Nickeisha A Stephenson; Lu Wang; Benjamin H Rotstein; Neil Vasdev; Pingping Tang; Steven H Liang
Journal:  Chem Commun (Camb)       Date:  2016-12-20       Impact factor: 6.222

6.  Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.

Authors:  Naish Lalloo; Christian A Malapit; S Maryamdokht Taimoory; Conor E Brigham; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2021-10-28       Impact factor: 15.419

7.  Copper-catalyzed carbo-difluoromethylation of alkenes via radical relay.

Authors:  Aijie Cai; Wenhao Yan; Xiaojun Zeng; Samson B Zacate; Tzu-Hsuan Chao; Jeanette A Krause; Mu-Jeng Cheng; Wei Liu
Journal:  Nat Commun       Date:  2021-06-01       Impact factor: 14.919

8.  3,3-Difluoroallyl ammonium salts: highly versatile, stable and selective gem-difluoroallylation reagents.

Authors:  Fei Ye; Yao Ge; Anke Spannenberg; Helfried Neumann; Li-Wen Xu; Matthias Beller
Journal:  Nat Commun       Date:  2021-05-31       Impact factor: 14.919

9.  Palladium-catalyzed difluoromethylation of heteroaryl chlorides, bromides and iodides.

Authors:  Changhui Lu; Yang Gu; Jiang Wu; Yucheng Gu; Qilong Shen
Journal:  Chem Sci       Date:  2017-04-24       Impact factor: 9.825

10.  Highly selective nickel-catalyzed gem-difluoropropargylation of unactivated alkylzinc reagents.

Authors:  Lun An; Chang Xu; Xingang Zhang
Journal:  Nat Commun       Date:  2017-11-13       Impact factor: 14.919
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