Issue 14, 2022

Visible light-induced Ni-catalyzed C–heteroatom cross-coupling of aryl halides via LMCT with DBU to access a Ni(i)/Ni(iii) cycle

Abstract

Cross-coupling of aryl halides with nucleophiles is a synthetically attractive strategy to construct C–heteroatom bonds. Here we report a highly efficient photoinduced Ni-catalyzed method for the C–heteroatom cross-coupling of aryl halides. The reaction proceeds smoothly in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under visible light irradiation and is distinct from that mediated by photoredox/nickel dual catalysis, requiring no external photosensitizers. A diverse range of nucleophiles, including amines, amides, sulfonamides, carboxylic acids, alcohols, thiophenols, phosphite and sodium sulfinate, are successfully coupled with electronically diverse aryl halides, presenting a universal approach for different C–heteroatom coupling reactions. Mechanistic studies suggest that a catalytically active Ni(I) species is generated via photoinduced ligand-to-metal charge transfer (LMCT) with DBU to access a Ni(I)/Ni(III) catalytic cycle.

Graphical abstract: Visible light-induced Ni-catalyzed C–heteroatom cross-coupling of aryl halides via LMCT with DBU to access a Ni(i)/Ni(iii) cycle

Supplementary files

Article information

Article type
Research Article
Submitted
14 Apr 2022
Accepted
01 Jun 2022
First published
06 Jun 2022

Org. Chem. Front., 2022,9, 3847-3853

Visible light-induced Ni-catalyzed C–heteroatom cross-coupling of aryl halides via LMCT with DBU to access a Ni(I)/Ni(III) cycle

R. Li, C. Yang, B. Niu, L. Li, J. Ma, Z. Li, H. Jiang and W. Cheng, Org. Chem. Front., 2022, 9, 3847 DOI: 10.1039/D2QO00607C

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