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:
yiyunchen
sioc.ac.cn
H. Huang, G. Zhang, L. Gong, S. Zhang, Y. Chen, J. Am. Chem. Soc., 2014, 136, 2280-2283.
DOI: 10.1021/ja412578t
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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.
see article for more examples
K. Jia, F. Zhang, H. Huang, Y. Chen, J. Am. Chem. Soc., 2016, 138, 1514-1517.
Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations
J. Borrel, J. Waser, Org. Lett., 2022, 24, 142-146.
Key Words
ID: J48-Y2014
