Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

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

Radical Borylation/Cyclization Cascade of 1,6-Enynes for the Synthesis of Boron-Handled Hetero- and Carbocycles
Shi-Chao Ren, Feng-Lian Zhang, Jing Qi, Ai-Qing Xu, Yi-Feng Wang, Yun-Shuai Huang, Hong-Yi Yan
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b01889

DOI: 10.1021/jacs.7b01889

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