Electrophotocatalytic Acetoxyhydroxylation of Aryl Olefins

He Huang; Tristan H. Lambert

doi:10.1021/jacs.1c01967

Electrophotocatalytic Acetoxyhydroxylation of Aryl Olefins

He Huang, Tristan H. Lambert^*

^*Corresponding author for this work

Cornell University

Research output: Contribution to journal › Article › peer-review

80 Citations (Scopus)

Abstract

A method for the acetoxyhydroxylation of olefins with syn stereoselectivity under electrophotocatalytic conditions is described. The procedure uses a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding glycol monoesters with high chemo- and diastereoselectivity. This reaction can be performed in batch or in flow, enabling multigram synthesis of the monoester products.

Original language	English
Pages (from-to)	7247-7252
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	143
Issue number	19
DOIs	https://doi.org/10.1021/jacs.1c01967
Publication status	Published - 19 May 2021
Externally published	Yes

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10.1021/jacs.1c01967

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abstract = "A method for the acetoxyhydroxylation of olefins with syn stereoselectivity under electrophotocatalytic conditions is described. The procedure uses a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding glycol monoesters with high chemo- and diastereoselectivity. This reaction can be performed in batch or in flow, enabling multigram synthesis of the monoester products.",

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N2 - A method for the acetoxyhydroxylation of olefins with syn stereoselectivity under electrophotocatalytic conditions is described. The procedure uses a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding glycol monoesters with high chemo- and diastereoselectivity. This reaction can be performed in batch or in flow, enabling multigram synthesis of the monoester products.

AB - A method for the acetoxyhydroxylation of olefins with syn stereoselectivity under electrophotocatalytic conditions is described. The procedure uses a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding glycol monoesters with high chemo- and diastereoselectivity. This reaction can be performed in batch or in flow, enabling multigram synthesis of the monoester products.

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Electrophotocatalytic Acetoxyhydroxylation of Aryl Olefins

Abstract

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