Radical Borylation/Cyclization Cascade of 1,6-Enynes for the Synthesis of Boron-Handled Hetero- and Carbocycles

A synthetic method to construct boron-handled cyclic molecules was developed based on a radical borylation/cyclization cascade of 1,6-enynes. The process was initiated by the chemo- and regio-controlled addition of an N-heterocyclic carbene–boryl radical to an alkene or alkyne, followed by ring clos...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-05, Vol.139 (17), p.6050-6053
Main Authors: Ren, Shi-Chao, Zhang, Feng-Lian, Qi, Jing, Huang, Yun-Shuai, Xu, Ai-Qing, Yan, Hong-Yi, Wang, Yi-Feng
Format: Article
Language:English
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Summary:A synthetic method to construct boron-handled cyclic molecules was developed based on a radical borylation/cyclization cascade of 1,6-enynes. The process was initiated by the chemo- and regio-controlled addition of an N-heterocyclic carbene–boryl radical to an alkene or alkyne, followed by ring closure to afford boron-substituted cyclic skeletons. Further molecular transformations of the cyclic products to synthetically useful building blocks were also demonstrated.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b01889