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Visible light driven, nickel-catalyzed aryl esterification using a triplet photosensitiser thioxanthen-9-one

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Abstract

We report an approach to the visible light-initiated, nickel-catalyzed esterification of carboxylic acids with aryl bromides. Thioxanthen-9-one works as a triplet photosensitizer to significantly accelerate this cross-coupling to provide aryl esters in moderate to excellent yields at room temperature. A mechanistic investigation indicates that this esterification undergoes the stepwise oxidative addition of an arylbromide to nickel, transmetalation of an aryl–Ni(II) bromide complex, energy transfer from thioxanthen-9-one to an excited-state aryl–Ni(II) carboxylate and reductive elimination to the aryl ester. This study contributes to the utilization of ketones as triplet photosensitisers in photochemical transformations.

Graphical abstract: Visible light driven, nickel-catalyzed aryl esterification using a triplet photosensitiser thioxanthen-9-one

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Publication details

The article was received on 22 Apr 2019, accepted on 15 May 2019 and first published on 16 May 2019


Article type: Research Article
DOI: 10.1039/C9QO00536F
Org. Chem. Front., 2019, Advance Article

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    Visible light driven, nickel-catalyzed aryl esterification using a triplet photosensitiser thioxanthen-9-one

    D. Zhu, H. Li, Z. Xu, H. Li, D. J. Young and J. Lang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00536F

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