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

Research output: Contribution to journalArticlepeer-review

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 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.

Original languageEnglish
Pages (from-to)1437-1444
Number of pages8
JournalOrganic Chemistry Frontiers
Volume9
Issue number5
DOIs
Publication statusPublished - 7 Mar 2022

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