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American Chemical Society, Journal of Organic Chemistry, 4(79), p. 1529-1541, 2014

DOI: 10.1021/jo402626u

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Ti/Ni-Mediated Inter- and Intramolecular Conjugate Addition of Aryl and Alkenyl Halides and Inflates

This paper is available in a repository.
This paper is available in a repository.

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Abstract

In this work we show that the unique combination of a nickel catalyst and Cp2TiCl allows the direct conjugate addition of aryl and alkenyl iodides, bromides and, in less extension, chlorides and triflates to alpha,beta-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional-group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five and six-membered rings are obtained in good yields. Moreover, some insights about the mechanism involved have been obtained from cyclic voltammetry, UV-Vis and HRTEM measurements.