Literature DB >> 29278333

Iron-Catalyzed Difluoromethylation of Arylzincs with Difluoromethyl 2-Pyridyl Sulfone.

Wenjun Miao1, Yanchuan Zhao1, Chuanfa Ni1, Bing Gao1, Wei Zhang1, Jinbo Hu1.   

Abstract

We report the first iron-catalyzed difluoromethylation of arylzincs with difluoromethyl 2-pyridyl sulfone via selective C-S bond cleavage. This method employs the readily available, bench-stable fluoroalkyl sulfone reagent and inexpensive iron catalyst, allowing facile access to structurally diverse difluoromethylated arenes at low temperatures. The experiment employing a radical clock indicates the involvement of radical species in this iron-catalyzed difluoromethylation process.

Entities:  

Year:  2018        PMID: 29278333     DOI: 10.1021/jacs.7b11976

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.  Generation of formaldehyde and formaldehyde-d2 for hydroxymethylations and hydroxydeuteromethylations of difluoroenolates and difluorobenzyl carbanions.

Authors:  Hari R Khatri; Changho Han; Reem A Alkhodier; Amna T Adam; Baharul Islam; David A Colby
Journal:  Chem Commun (Camb)       Date:  2022-05-03       Impact factor: 6.065

3.  Radical Retrosynthesis.

Authors:  Joel M Smith; Stephen J Harwood; Phil S Baran
Journal:  Acc Chem Res       Date:  2018-08-02       Impact factor: 22.384

4.  Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers.

Authors:  Samantha A Green; Suhelen Vásquez-Céspedes; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-07-26       Impact factor: 15.419

5.  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

6.  A TMEDA-Iron Adduct Reaction Manifold in Iron-Catalyzed C(sp2 )-C(sp3 ) Cross-Coupling Reactions.

Authors:  Nikki J Bakas; Jeffrey D Sears; William W Brennessel; Michael L Neidig
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-18       Impact factor: 15.336

7.  Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel.

Authors:  Chang Xu; Wen-Hao Guo; Xu He; Yin-Long Guo; Xue-Ying Zhang; Xingang Zhang
Journal:  Nat Commun       Date:  2018-03-21       Impact factor: 14.919

8.  Cobalt-catalyzed difluoroalkylation of tertiary aryl ketones for facile synthesis of quaternary alkyl difluorides.

Authors:  Chao Li; Yi-Xuan Cao; Rui Wang; Yi-Ning Wang; Quan Lan; Xi-Sheng Wang
Journal:  Nat Commun       Date:  2018-11-23       Impact factor: 14.919

9.  Chlorodifluoromethane as a C1 Synthon in the Assembly of N-Containing Compounds.

Authors:  Xingxing Ma; Jianke Su; Xingang Zhang; Qiuling Song
Journal:  iScience       Date:  2019-07-08

10.  Highly stereoselective nickel-catalyzed difluoroalkylation of aryl ketones to tetrasubstituted monofluoroalkenes and quaternary alkyl difluorides.

Authors:  Chao Li; Yi-Xuan Cao; Ruo-Xing Jin; Kang-Jie Bian; Zi-Yang Qin; Quan Lan; Xi-Sheng Wang
Journal:  Chem Sci       Date:  2019-08-20       Impact factor: 9.825

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