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

Da Liang Zhu, Hong Xi Li, Ze Ming Xu, Hai Yan Li, David J. Young, Jian Ping Lang

Research output: Contribution to journalArticleResearchpeer-review

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.

Original languageEnglish
Pages (from-to)2353-2359
Number of pages7
JournalOrganic Chemistry Frontiers
Volume6
Issue number14
Early online date16 May 2019
DOIs
Publication statusPublished - 21 Jul 2019

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Photosensitizing Agents
Esterification
Nickel
Bromides
Esters
Carboxylic Acids
Ketones
Excited states
Energy transfer
Temperature

Cite this

Zhu, Da Liang ; Li, Hong Xi ; Xu, Ze Ming ; Li, Hai Yan ; Young, David J. ; Lang, Jian Ping. / Visible light driven, nickel-catalyzed aryl esterification using a triplet photosensitiser thioxanthen-9-one. In: Organic Chemistry Frontiers. 2019 ; Vol. 6, No. 14. pp. 2353-2359.
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Visible light driven, nickel-catalyzed aryl esterification using a triplet photosensitiser thioxanthen-9-one. / Zhu, Da Liang; Li, Hong Xi; Xu, Ze Ming; Li, Hai Yan; Young, David J.; Lang, Jian Ping.

In: Organic Chemistry Frontiers, Vol. 6, No. 14, 21.07.2019, p. 2353-2359.

Research output: Contribution to journalArticleResearchpeer-review

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