Copper-Catalyzed Bromodifluoroacetylative Cyclization of Enynes

A copper-catalyzed bromodifluoroacetylative cyclization reaction is described. The treatment of bromodifluoroacete derivatives by CuI and B2Pin2 enables difluoroalkyl radical generation and triggers the radical addition/cyclization/bromination sequences. Bromodifluoroacetyl-derived ester, amide, and...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-12, Vol.85 (23), p.15667-15675
Main Authors: Zhu, Shaoqun, Yang, Haibo, Jiang, Along, Zhou, Bing, Han, Ying, Yan, Chaoguo, Shi, Yaocheng, Hou, Hong
Format: Article
Language:English
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Summary:A copper-catalyzed bromodifluoroacetylative cyclization reaction is described. The treatment of bromodifluoroacete derivatives by CuI and B2Pin2 enables difluoroalkyl radical generation and triggers the radical addition/cyclization/bromination sequences. Bromodifluoroacetyl-derived ester, amide, and ketone were compatible and gave various vinyl C–Br bonds containing functionalized heterocycles in good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02114