Photoredox-mediated remote C(sp3)-H heteroarylation of free alcohols

Guo Xing Li; Xiafei Hu; Gang He; Gong Chen

doi:10.1039/c8sc04134b

Photoredox-mediated remote C(sp³)-H heteroarylation of free alcohols

Guo Xing Li, Xiafei Hu, Gang He, Gong Chen

Chemistry

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

134 Scopus citations

Abstract

We report an efficient and economical method for remote δ C(sp³)-H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C-C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.

Original language	English (US)
Pages (from-to)	688-693
Number of pages	6
Journal	Chemical Science
Volume	10
Issue number	3
DOIs	https://doi.org/10.1039/c8sc04134b
State	Published - 2019

All Science Journal Classification (ASJC) codes

General Chemistry

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abstract = "We report an efficient and economical method for remote δ C(sp3)-H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C-C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.",

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AU - Li, Guo Xing

AU - Hu, Xiafei

AU - He, Gang

AU - Chen, Gong

PY - 2019

Y1 - 2019

N2 - We report an efficient and economical method for remote δ C(sp3)-H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C-C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.

AB - We report an efficient and economical method for remote δ C(sp3)-H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C-C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.

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JO - Chemical Science

JF - Chemical Science

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Photoredox-mediated remote C(sp³)-H heteroarylation of free alcohols

Abstract

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