Citation: Junxin Li, Chao Chen, Yuzhen Dong, Jian Lv, Jun-Mei Peng, Yuan-Ye Jiang, Daoshan Yang. Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis[J]. Chinese Chemical Letters, ;2024, 35(11): 109732. doi: 10.1016/j.cclet.2024.109732 shu

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

Junxin Li ^{a, 1} ,
Chao Chen ^{b, 1} ,
Yuzhen Dong ^a ,
Jian Lv ^a ,
Jun-Mei Peng ^c ,
Yuan-Ye Jiang ^{b, *,} ,
Daoshan Yang ^{a, *,}

a.
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
b.
Laboratory of Catalytic Conversion and Clean Energy in Universities of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China
c.
Department of Medicinal Chemistry, School of Pharmacy, Hengyang Medical School, University of South China, Hengyang 421001, China

yuanyejiang@qfnu.edu.cn

yangdaoshan@tsinghua.org.cn

Received Date: 26 December 2023
Revised Date: 1 February 2024
Accepted Date: 19 February 2024
Available Online: 8 March 2024

Figures(6)

Developing applicable methods to forge linkages between sp³ and sp²-hydridized carbons is of great significance 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 computational mechanistic studies support LNi^ⅠAr as an active species, while the untraditional anti-Markovnikov selective alkylation of asymmetric sulfonium salts is determined by the oxidative S-substitution of sulfonium salts with LNi^ⅠAr. 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.
- Reductive cross-coupling reaction,
- Csp³−Csp² bonds,
- Nickel catalysis,
- Sulfonium salts,
- Alkylation
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