Transition-metal-free cross-coupling of indium organometallics with chromene and isochroman acetals mediated by BF3·OEt2
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Transition-metal-free cross-coupling of indium organometallics with chromene and isochroman acetals mediated by BF3·OEt2Date
2016Citation
Transition-Metal-Free Cross-Coupling of Indium Organometallics with Chromene and Isochroman Acetals Mediated by BF3·OEt2. José M. Gil-Negrete, José Pérez Sestelo, and Luis A. Sarandeses. Organic Letters 2016 18 (17), 4316-4319.
Abstract
[Abstract] A transition-metal-free coupling of triorganoindium reagents with benzopyranyl acetals mediated by a Lewis acid has been developed. The reaction of R3In with chromene and isochroman acetals in the presence of BF3·OEt2 afforded 2-substituted chromenes and 1-substituted isochromans, respectively, in good yields. The reactions proceed with a variety of triorganoindium reagents (aryl, heteroaryl, alkynyl, alkenyl, alkyl) using only 50 mol % of the organometallic, thus demonstrating the efficiency of these species. Preliminary mechanistic studies indicate the formation of an oxocarbenium ion intermediate in the presence of the Lewis acid.
Keywords
Indium organometallics
Carbon-carbon bond forming reactions
Transition-metal-free reactions
Carbon-carbon bond forming reactions
Transition-metal-free reactions
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Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher.
ISSN
1523-7060