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Visible-light mediated cross-coupling of aryl halides with sodium sulfinates via carbonyl-photoredox/nickel dual catalysis†
Shan Jiang,Zi-Tong Zhang,David James Young,Lu-Lu Chai,Qi Wu,Hong-Xi Li
Organic Chemistry Frontiers Pub Date : 01/25/2022 00:00:00 , DOI:10.1039/D1QO01850G
Abstract

Photoinduced nickel-catalyzed cross-coupling of arylsulfinates (ArSO2) with (hetero)aryl halides (Ar′–X) via visible light photoexcitation of 2-chloro-thioxanthen-9-one (Cl-TXO) has been achieved in moderate to excellent yields. This photocoupling exhibited a broad substrate scope with good functional group tolerance to give diarylsulfones. The mechanism involves oxidative addition of Ar′–X to Ni(0), oxidation with Image ID:d1qo01850g-t1.gif derived from single-electron-oxidation of ArSO2 by photoexcited Cl-TXO*, reductive elimination and release of the product diaryl sulfone and NiI catalyst. The photoredox and nickel catalytic cycles interact through electron transfer from the single-electron-reduced Cl-TXO ([Cl-TXO]˙) to the NiI species.

Graphical abstract: Visible-light mediated cross-coupling of aryl halides with sodium sulfinates via carbonyl-photoredox/nickel dual catalysis
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