Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins

He Huang; Tristan H. Lambert

doi:10.1021/jacs.2c08951

Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins

He Huang, Tristan H. Lambert^*

^*Corresponding author for this work

Cornell University

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

31 Citations (Scopus)

Abstract

A method for the regiodivergent aminooxygenation of aryl olefins under electrophotocatalytic conditions is described. The procedure employs a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding oxazolines with high chemo- and diastereoselectivity. With the judicious choice between two inexpensive and abundant reagents, namely water and urethane, either 2-amino-1-ol or 1-amino-2-ol derivatives could be prepared from the same substrate. This method is amenable to multigram synthesis of the oxazoline products with low catalyst loadings.

Original language	English
Pages (from-to)	18803-18809
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	144
Issue number	41
DOIs	https://doi.org/10.1021/jacs.2c08951
Publication status	Published - 19 Oct 2022
Externally published	Yes

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10.1021/jacs.2c08951

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abstract = "A method for the regiodivergent aminooxygenation of aryl olefins under electrophotocatalytic conditions is described. The procedure employs a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding oxazolines with high chemo- and diastereoselectivity. With the judicious choice between two inexpensive and abundant reagents, namely water and urethane, either 2-amino-1-ol or 1-amino-2-ol derivatives could be prepared from the same substrate. This method is amenable to multigram synthesis of the oxazoline products with low catalyst loadings.",

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N2 - A method for the regiodivergent aminooxygenation of aryl olefins under electrophotocatalytic conditions is described. The procedure employs a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding oxazolines with high chemo- and diastereoselectivity. With the judicious choice between two inexpensive and abundant reagents, namely water and urethane, either 2-amino-1-ol or 1-amino-2-ol derivatives could be prepared from the same substrate. This method is amenable to multigram synthesis of the oxazoline products with low catalyst loadings.

AB - A method for the regiodivergent aminooxygenation of aryl olefins under electrophotocatalytic conditions is described. The procedure employs a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding oxazolines with high chemo- and diastereoselectivity. With the judicious choice between two inexpensive and abundant reagents, namely water and urethane, either 2-amino-1-ol or 1-amino-2-ol derivatives could be prepared from the same substrate. This method is amenable to multigram synthesis of the oxazoline products with low catalyst loadings.

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EP - 18809

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 41

ER -

Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins

Abstract

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