Organic Chemistry Portal

Abstracts

Search:

Cobalt-Catalyzed Carbozincation of Ynamides

Romain Sallio, Martin Corpet, Loic Habert, Muriel Durandetti, Corinne Gosmini* and Isabelle Gillaizeau*

*Université Paris Saclay, 91128 Palaiseau Cedex; Université d’Orléans, rue de Chartres, 45100 Orléans, France, Email: corinne.gosminipolytechnique.edu, isabelle.gillaizeauuniv-orleans.fr

R. Sallio, M. Corpet, L. Habert, M. Durandetti, C. Gosmini, I. Gillaizeau, J. Org. Chem., 2017, 82, 1254-1259.

DOI: 10.1021/acs.joc.6b02612 (free Supporting Information)


see abstract for more reactions

Abstract

A cobalt-catalyzed ynamide carbozincation provides diverse 3-aryl enamides with mild reaction conditions and good functional-group tolerance. This reaction displays an excellent regio- and total stereoselectivity. Moreover, this approach allows the selective synthesis of biologically relevant 3,5-disubstituted oxazolone frameworks.

see article for more examples


proposed mechanism



Key Words

arylation


ID: J42-Y2017