Brønsted Acid Catalyzed α′-Functionalization of Silylenol Ethers with Indoles

A new method which enables carbon–carbon bond formation at the α′‐position of silylenol ethers by using catalytic amounts of pyridinium triflate is reported. This chemistry successfully produces, structurally challenging, highly substituted indole‐containing silylenol ethers in excellent yields with...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-04, Vol.54 (15), p.4641-4645
Main Authors: Ayala, Caitlan E., Dange, Nitin S., Fronczek, Frank R., Kartika, Rendy
Format: Article
Language:English
Subjects:
Brønsted acid
heterocycles
nucleophilic substitution
oxyallyl cations
silylenol ethers
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Summary:A new method which enables carbon–carbon bond formation at the α′‐position of silylenol ethers by using catalytic amounts of pyridinium triflate is reported. This chemistry successfully produces, structurally challenging, highly substituted indole‐containing silylenol ethers in excellent yields with complete regiocontrol, presumably through silyloxyallyl cation intermediates. Despite the use of Brønsted acid, the silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions. Under control: The title reaction enables CC bond formation at the α′‐position of silylenol ethers. Highly substituted indole‐containing silylenol ethers are generated in excellent yields with complete regiocontrol presumably through silyloxyallyl cation intermediates. The silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201409758