Gold(I)-catalyzed cycloisomerization-dimerization cascade of benzene-tethered 1,6-enynes

Monica Alvarez-Perez (1) , Maria Frutos (1, 2) , Alma Viso (1, 2) , Roberto Fernandez de La Pradilla (1, 2) , Maria C. de La Torre (1, 2) , Miguel A. Sierra (3, 2) , Heinz Gornitzka (4, 5) , Catherine Hemmert (4)

1 CSIC-IQOG
2 ORFEO−CINQA - Centro de Innovación en Química Avanzada (ORFEO−CINQA Network)
3 Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense
4 LCC - Laboratoire de chimie de coordination
5 UT3 - Université Toulouse III - Paul Sabatier

An unprecedented stereoselective domino reaction of 1,6-enynes with an aryl ring at C3–C4 in the presence of gold(I) catalysts at low temperature is described. This process involves a novel 5-exo-dig cycloisomerization–dimerization sequence to afford formal Diels–Alder adducts that undergo a smooth gold-catalyzed double bond migration at room temperature. In addition, the first examples of the gold mesoionic carbene mediated [2+2+2] cycloaddition of these enynes with benzaldehyde are reported.

Mots clés: Mixtures; Carbene compounds; Catalysts; Chemical reactions; Cyclization

Domaines: Chimie de coordination

Monica Alvarez-Perez, Maria Frutos, Alma Viso, Roberto Fernandez de La Pradilla, Maria C. de La Torre, et al.. Gold(I)-catalyzed cycloisomerization-dimerization cascade of benzene-tethered 1,6-enynes. Journal of Organic Chemistry, 2017, 82 (14), pp.7546-7554. ⟨10.1021/acs.joc.7b01273⟩. ⟨hal-01947828⟩