Visible-light mediated cross-coupling of aryl halides with sodium sulfinates via carbonyl-photoredox/nickel dual catalysis. Issue 5 (4th February 2022)

• Record Type: Journal Article
• Authors: Jiang, Shan; Zhang, Zi-Tong; Young, David James; Chai, Lu-Lu; Wu, Qi; Li, Hong-Xi
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 5(2022)
• Page Start: 1437
• Page End: 1444
• Publication Date: 2022-02-04
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01850g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The nickel-catalyzed arylsulfonylation of aryl bromides using 2-chloro-thioxanthen-9-one as a photoredox catalyst under visible light provided diaryl sulfones in moderate to excellent yields. 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 Ni I catalyst. The photoredox and nickel catalytic cycles interact through electron transfer from the single-electron-reduced Cl-TXO ([Cl-TXO]˙ − ) to the Ni I species.