Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp³)-C(sp³) Bond Cleavage and Functionalizations

Kunfang Jia, Fuyuan Zhang, Hanchu Huang and Yiyun Chen*

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: yiyunchensioc.ac.cn

K. Jia, F. Zhang, H. Huang, Y. Chen, J. Am. Chem. Soc., 2016, 138, 1514-1517.

DOI: 10.1021/jacs.5b13066

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Abstract

A visible-light-induced oxidation of alcohols generates alkoxyl radicals mediated by iodine(III) reagents under mild reaction conditions. The β-fragmentation of alkoxyl radicals enables selective C(sp³)-C(sp³) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols and linear alcohols.

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Visible-Light-Induced Chemoselective Deboronative Alkynylation under Biomolecule-Compatible Conditions

H. Huang, G. Zhang, L. Gong, S. Zhang, Y. Chen, J. Am. Chem. Soc., 2014, 136, 2280-2283.

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Key Words

alkynylation, carbonyl compounds, hypervalent iodine compounds

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ID: J48-Y2016