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Published on: April 22, 2016
γ-Alkylation of Alcohols Enabled by Visible-Light Induced 1,6-Hydrogen Atom Transfer
Wei Shu1,2, Hui Zhang1, Yan Huang1
1Department of Chemistry and Shenzhen Grubbs Institute , Southern University of Science and Technology , 518055 , Shenzhen , Guangdong , China.
Abstract:
Site-selective remote alkylation of alcohol is attractive but challenging in organic synthesis. Herein, we report a novel visible-light mediated γ-alkylation of alcohol derivatives via the formation of Csp3-Csp3 bond through Csp3-H bond functionalization under mild conditions. The use of sulfamate esters enables the directed, otherwise rare 1,6-HAT to generate γ-selective C-centered radical, which is complementary to δ-selective 1,5-HAT of alcohols. This redox-neutral protocol provides a general and operationally simple method to access γ-alkylated alcohols.
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