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

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 temperatur...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 14; pp. 2353 - 2359
Main Authors Zhu, Da-Liang, Li, Hong-Xi, Xu, Ze-Ming, Li, Hai-Yan, Young, David J., Lang, Jian-Ping
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2019
Royal Society of Chemistry
Subjects
Aromatic compounds
Bromides
Carboxylic acids
Chemistry
Chemistry, Organic
Cross coupling
Energy transfer
Esterification
Esters
Ketones
Nickel
NMR
Nuclear magnetic resonance
Organic chemistry
Photochemicals
Physical Sciences
Science & Technology
METAL-FREE SYNTHESIS
ACTIVATION
2+2 PHOTOCYCLOADDITION
ESTERS
COMPLEXES
ARYLATION
CARBOXYLIC-ACIDS
PHOTOREDOX CATALYSIS
TRIFLUOROMETHYLATION
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Summary: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.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo00536f