Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis

Wenxin Chen; Zheng Liu; Jiaqi Tian; Jin Li; Jing Ma; Xu Cheng; Guigen Li

doi:10.1021/jacs.6b06379

Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis

Wenxin Chen, Zheng Liu, Jiaqi Tian, Jin Li, Jing Ma, Xu Cheng, Guigen Li

Chemistry and Biochemistry

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

94 Scopus citations

Abstract

For the first time, 4-alkyl Hantzsch esters were used to construct molecules with all-carbon quaternary centers by visible light-induced photoredox catalysis via transfer alkylation. Up to a 1500 h^-1 turnover frequency was achieved in this reaction. Reactions of 4-alkyl Hantzsch nitriles as tertiary radical donors joined two contiguous all-carbon quaternary centers intermolecularly, and this chemistry was used to synthesize a common precursor of a class of hydroxysteroid dehydrogenase inhibitors.

Original language	English
Pages (from-to)	12312-12315
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	38
DOIs	https://doi.org/10.1021/jacs.6b06379
State	Published - Sep 28 2016

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abstract = "For the first time, 4-alkyl Hantzsch esters were used to construct molecules with all-carbon quaternary centers by visible light-induced photoredox catalysis via transfer alkylation. Up to a 1500 h-1 turnover frequency was achieved in this reaction. Reactions of 4-alkyl Hantzsch nitriles as tertiary radical donors joined two contiguous all-carbon quaternary centers intermolecularly, and this chemistry was used to synthesize a common precursor of a class of hydroxysteroid dehydrogenase inhibitors.",

author = "Wenxin Chen and Zheng Liu and Jiaqi Tian and Jin Li and Jing Ma and Xu Cheng and Guigen Li",

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T2 - Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis

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AU - Liu, Zheng

AU - Tian, Jiaqi

AU - Li, Jin

AU - Ma, Jing

AU - Cheng, Xu

AU - Li, Guigen

PY - 2016/9/28

Y1 - 2016/9/28

N2 - For the first time, 4-alkyl Hantzsch esters were used to construct molecules with all-carbon quaternary centers by visible light-induced photoredox catalysis via transfer alkylation. Up to a 1500 h-1 turnover frequency was achieved in this reaction. Reactions of 4-alkyl Hantzsch nitriles as tertiary radical donors joined two contiguous all-carbon quaternary centers intermolecularly, and this chemistry was used to synthesize a common precursor of a class of hydroxysteroid dehydrogenase inhibitors.

AB - For the first time, 4-alkyl Hantzsch esters were used to construct molecules with all-carbon quaternary centers by visible light-induced photoredox catalysis via transfer alkylation. Up to a 1500 h-1 turnover frequency was achieved in this reaction. Reactions of 4-alkyl Hantzsch nitriles as tertiary radical donors joined two contiguous all-carbon quaternary centers intermolecularly, and this chemistry was used to synthesize a common precursor of a class of hydroxysteroid dehydrogenase inhibitors.

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