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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Published inJournal of the American Chemical Society Vol. 139; no. 17; pp. 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 Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.05.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
HYDROGEN
ALKENES
HYDROBORATION
CARBENE-BORYL RADICALS
RATE CONSTANTS
PHOTOPOLYMERIZATIONS
SUBSTITUTION-REACTIONS
BORANES
ALKYNES
POLARITY-REVERSAL CATALYSIS
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b01889