Synthesis 2016; 48(19): 3373-3381
DOI: 10.1055/s-0035-1562460
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Silylcupration of Activated Alkynes

Sébastien Vercruysse
a   Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST), Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium   eMail: olivier.riant@uclouvain.be
,
Kévin Jouvin
b   Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin-en-Yvelines, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France
,
Olivier Riant*
a   Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST), Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium   eMail: olivier.riant@uclouvain.be
,
Gwilherm Evano*
c   Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   eMail: gevano@ulb.ac.be
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Publikationsverlauf

Received: 15. Juni 2016

Accepted after revision: 16. Juni 2016

Publikationsdatum:
08. August 2016 (online)


Dedicated to the memory of Jean Normant, a wonderful man and a truly inspiring chemist

Abstract

A highly efficient catalytic silylcupration of activated alkynes is reported. Upon reaction with silylboronates and methanol in THF at room temperature in the presence of copper(I) fluoride tris(triphenylphosphine), a range of ynamides and propiolates were found to undergo a smooth silylcupration. This reaction, which tolerates various functional groups, affords a straightforward and efficient entry to the corresponding β-silylenamides and -acrylates, which were formed with high levels of regio- and stereoselectivities.

Supporting Information

 
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