Reactions of alkenes and alkynes with formaldehyde catalyzed by rhodium systems containing phosphine ligands

Merlín Rosales, Beatriz González, Jessely Molina, Homero Pérez, María Modroño-Alonso, Pablo J. Baricelli

Abstract


The reaction of alkenes (allyl alcohol, styrene and C6 alkenes) with formaldehyde was efficiently performed by using Rh precatalysts formed in situ by the addition of triphenylphosphine (PPh3), 1,2-bis(diphenylphosphino)ethane (dppe) or 1,1,1-tris(diphenylphosphinomethyl) ethane (triphos) to the complex Rh(acac)(CO)2 at 130ºC in 1,4-dioxane, yielding their corresponding aldehydes; the best catalytic system was Rh(acac)(CO)2/2dppe, which generates the cationic complex [Rh(k2-P,P-dppe)2]+. However, the reaction of phenylacetylene with formaldehyde under the same reaction conditions generated styrene, which was found to be the product of transfer hydrogenation from formaldehyde.

Keywords


hydroformylation; formaldehyde; alkenes; alkynes; rhodium; phosphine.

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Copyright (c) 2017 Merlín Rosales, Beatriz González, Jessely Molina, Homero Pérez, María Modroño-Alonso, Pablo J. Baricelli

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Journal of the Mexican Chemical Society (J. Mex. Chem. Soc.) Vol 61, No 3 (2017). Quarterly publication (July-September). Edited and distributed by Sociedad Química de México, A.C. Barranca del Muerto 26, Col. Crédito Constructor, Del. Benito Juárez, C.P. 03940, Mexico City. Phone: +5255 56626837; +5255 56626823 Contact: soquimex@sqm.org.mx http://www.sqm.org.mx Editor-in-Chief: Ignacio González-Martínez. Indexed Journal. Certificate of reserved rights granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 04-2005-052710530600-102. Certificate of lawful title and content: Under procedure. ISSN-e granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 2594-0317. ISSN granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 1870-249X. Postal registration of printed matter deposited by editors or agents granted by SEPOMEX: IM09-0312 Copyright © Sociedad Química de México, A.C. Total or partial reproduction is prohibited without written permission of the right holder. The Figures/schemes quality and the general contents of this publication are full responsibility of the authors. Updated October 26th, 2017 by Adriana Vázquez (editorial assistant, e-mail: editor.jmcs@gmail.com), J. Mex. Chem. Soc., Sociedad Química de México, A.C.