B(C6F5)3‐Catalyzed Ring Opening and Isomerization of Unactivated Cyclopropanes

Catalytic amounts of B(C6F5)3 promote the ring opening and subsequent isomerization of a series of unactivated cyclopropanes to afford terminal olefins in good yields when a hydrosilane and 2,6‐dibromopyridine are employed as additives. Opening inert cyclopropanes: B(C6F5)3‐catalyzed ring‐opening an...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-03, Vol.56 (14), p.4028-4032
Main Authors: Zhang, Zi‐Yu, Liu, Zhi‐Yun, Guo, Rui‐Ting, Zhao, Yu‐Quan, Li, Xiang, Wang, Xiao‐Chen
Format: Article
Language:English
Subjects:
Additives
Alkenes
boron
carbocations
Catalysis
C−C activation
Isomerization
Organic compounds
Ring opening
strained molecules
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Summary:Catalytic amounts of B(C6F5)3 promote the ring opening and subsequent isomerization of a series of unactivated cyclopropanes to afford terminal olefins in good yields when a hydrosilane and 2,6‐dibromopyridine are employed as additives. Opening inert cyclopropanes: B(C6F5)3‐catalyzed ring‐opening and isomerization reactions of aryl‐, alkyl‐, and vinyl‐substituted cyclopropanes are described. These reactions generate terminal olefins after a sequential process of C−C bond cleavage, 1,2‐hydride migration, and B(C6F5)3 dissociation. The addition of 2,6‐dibromopyridine and Ph3SiH is crucial for the reactivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201700864