Visible light-induced Ni-catalyzed C–heteroatom cross-coupling of aryl halides via LMCT with DBU to access a Ni(i)/Ni(iii) cycle. Issue 14 (15th June 2022)

• Record Type: Journal Article
• Authors: Li, Rui; Yang, Chen-Xi; Niu, Bai-Hua; Li, Li-Juan; Ma, Ji-Mei; Li, Zi-Long; Jiang, Hong; Cheng, Wan-Min
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 14(2022)
• Page Start: 3847
• Page End: 3853
• Publication Date: 2022-06-15
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00607c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A Ni-catalyzed C–heteroatom cross-coupling of aryl halides is reported by employing photoinduced LMCT with DBU. The reaction proceeds under visible light irradiation without an external photosensitizer and involves a variety of nucleophiles. 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.