中国化学快报(英文版)2024,Vol.35Issue(11) :349-354.DOI:10.1016/j.cclet.2024.109732

Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis

Junxin Li Chao Chen Yuzhen Dong Jian Lv Jun-Mei Peng Yuan-Ye Jiang Daoshan Yang
中国化学快报(英文版)2024,Vol.35Issue(11) :349-354.DOI:10.1016/j.cclet.2024.109732

Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis

Junxin Li 1Chao Chen 2Yuzhen Dong 1Jian Lv 1Jun-Mei Peng 3Yuan-Ye Jiang 2Daoshan Yang1
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作者信息

  • 1. Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science,MOE,College of Chemistry and Molecular Engineering,Qingdao University of Science and Technology,Qingdao 266042,China
  • 2. Laboratory of Catalytic Conversion and Clean Energy in Universities of Shandong Province,School of Chemistry and Chemical Engineering,Qufu Normal University,Qufu 273165,China
  • 3. Department of Medicinal Chemistry,School of Pharmacy,Hengyang Medical School,University of South China,Hengyang 421001,China
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Abstract

Developing applicable methods to forge linkages between sp3 and sp2-hydridized carbons is of great sig-nificance in drug discovery.We show here a new,Ni-catalyzed reductive cross-coupling reaction that forms Csp3-Csp2 bonds from aryl iodides and cyclic sulfonium salts.Notably,Csp3-Csp2 bonds can be forged selectively at the iodine-bearing carbon of bromo(iodo)arenes which is usually recognized as a huge challenge under the catalytic reductive cross-coupling(CRCC)conditions.Experimental and compu-tational mechanistic studies support LNiIAr as an active species,while the untraditional anti-Markovnikov selective alkylation of asymmetric sulfonium salts is determined by the oxidative S-substitution of sul-fonium salts with LNiIAr.This protocol further expands the range of alkyl electrophiles under the CRCC conditions and provides a new strategy for the construction of Csp3-Csp2 bonds.

Key words

Reductive cross-coupling reaction/Csp3-Csp2 bonds/Nickel catalysis/Sulfonium salts/Alkylation

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出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

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影响因子:0.771
ISSN:1001-8417
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