Nickel-catalyzed fluoroethylation of arylboronic acids via Suzuki-type coupling
Literature Information
Publication Date
2019-03-14
DOI
10.1039/C9QO00066F
Impact Factor
5.281
Authors
Yi Yang, Junjie Cai, Gen Luo, Yan Jiang, Yumei Su, Yang Su, Chaolin Li, Yubin Zheng, Jijiao Zeng, Yingle Liu
View Original
Abstract
A mild method for efficient access to fluoroethylated (hetero)arenes via Suzuki-type coupling has been developed. This base metal Ni-catalyzed method features selective transformation of the more susceptible C–X bond of 1-fluoro-2-haloethanes (FCH2CH2X, X = I or Br) and leaves the vicinal fluorine intact. Preliminary mechanistic studies illustrate the intermediacy of fluoroethyl radicals in the radical-rebound oxidative addition and Ni–B transmetalation as the rate-limiting step within the catalytic cycle. The practical value of this protocol is further demonstrated by late-stage modification of several complex bioactive molecules.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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Oxalic acid compound with cyclohexylsulfamothioic O-acid (11)
CAS Number:
31895-22-4
Molecular Formula:
C7H13NO4S3
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