Au^I-Catalyzed Hydroalkynylation of Haloalkynes

Pedro D. García-Fernández, Javier Iglesias-Sigüenza, Paula S. Rivero-Jerez, Elena Díez*, Enrique Gómez-Bengoa*, Rosario Fernández* and José M. Lassaletta*

*Universidad de Sevilla, Sevilla 41012; Universidad del Paı́s Vasco, San Sebastián 20080 Spain, Email: ediezus.es, enrique.gomezehu.es, ffernanus.es, jmlassaiiq.csic.es

P. D. García-Fernández, J. Iglesias-Sigüenza, P. S. Rivero-Jerez, E. Díez, E. Gómez-Bengoa, R. Fernández, J. M. Lassaletta, J. Am. Chem. Soc., 2020, 142, 16082-16089.

DOI: 10.1021/jacs.0c07951

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Abstract

Cationic Au complexes containing strongly basic NHC ligands and noncoordinating anions such as BAr^F₄ catalyze a cis haloalkynylation between terminal alkynes and aromatic haloalkynes, whereas introduction of a weakly basic triflate counteranion results in the stereoselective hydroalkynylation of the haloalkyne, yielding haloenyne products in good yields and complete trans selectivity.

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Key Words

enynes, bromoalkenes

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ID: J48-Y2020