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

Hanchu Huang, Guojin Zhang, Li Gong, Shuaiyan Zhang and Yiyun Chen*

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

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

DOI: 10.1021/ja412578t (free Supporting Information)


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Abstract

A redox-neutral and highly chemoselective visible-light-induced deboronative alkynylation reaction works with primary, secondary and tertiary alkyl trifluoroborates or boronic acids to generate aryl, alkyl and silyl substituted alkynes. This reaction tolerates substrates containing alkenes, alkynes, aldehydes, ketones, esters, nitriles, azides, aryl halides, alkyl halides, alcohols, and indoles.

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

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


Key Words

alkynylation


ID: J48-Y2014