A straightforward synthesis of a library of largely new 3-vinylindoles via a clean dehydrative coupling reaction between ketones and indoles has been developed. Highly stable, non-nucleophilic aryl(2-methylindol-3-yl)methylium salts have been used as efficient Lewis acid catalysts. The advantages of the reaction are the use of equimolar amounts of inexpensive and easily available reagents, the low catalyst amount, high atom efficiency, the production of only one molecule of water as a by-product and the mild reaction conditions. Computational studies of two specific reaction mechanism instances show that both steric and electronic effects heavily influence the nature of the final products, whether a methyl group in position 2 of the indole is present or absent.

A simple, direct synthesis of 3-vinylindoles from the carbocation-catalysed dehydrative cross-coupling of ketones and indoles. A combined experimental and computational study

Barbero, Margherita;Dughera, Stefano;Ghigo, Giovanni
2019-01-01

Abstract

A straightforward synthesis of a library of largely new 3-vinylindoles via a clean dehydrative coupling reaction between ketones and indoles has been developed. Highly stable, non-nucleophilic aryl(2-methylindol-3-yl)methylium salts have been used as efficient Lewis acid catalysts. The advantages of the reaction are the use of equimolar amounts of inexpensive and easily available reagents, the low catalyst amount, high atom efficiency, the production of only one molecule of water as a by-product and the mild reaction conditions. Computational studies of two specific reaction mechanism instances show that both steric and electronic effects heavily influence the nature of the final products, whether a methyl group in position 2 of the indole is present or absent.
2019
75
3
363
373
3-Vinylindoles, Dehydrative coupling, DFT calculations, Lewis acid catalysis, Stable carbocations,
Barbero, Margherita; Dughera, Stefano; Alberti, Sara; Ghigo, Giovanni
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1686828
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