CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1225-1234
DOI: 10.1055/s-0037-1611673
paper
Copyright with the author

Copper-Catalysed Hydroamination of N-Allenylsulfonamides: The Key Role of Ancillary Coordinating Groups

Rémi Blieck
a  Ecole Nationale Supérieure de Chimie de Montpellier, Institut Charles Gerhardt Montpellier UMR 5253 CNRS, AM2N, 8 rue de l’Ecole Normale, Montpellier 34296 Cedex 5   France   Email: florian.monnier@enscm.fr   Email: marc.taillefer@enscm.fr
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b  Chimie ParisTech, PSL University, CNRS, Institut de Recherche de Chimie Paris (IRCP), 75005 Paris, France   Email: luca.perego@ens.fr
c  PASTEUR, Département de Chimie, École Normale Supérieure, PSL University, Sorbonne Université, CNRS, 75005 Paris, France   Email: laurence.grimaud@ens.fr
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b  Chimie ParisTech, PSL University, CNRS, Institut de Recherche de Chimie Paris (IRCP), 75005 Paris, France   Email: luca.perego@ens.fr
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c  PASTEUR, Département de Chimie, École Normale Supérieure, PSL University, Sorbonne Université, CNRS, 75005 Paris, France   Email: laurence.grimaud@ens.fr
,
a  Ecole Nationale Supérieure de Chimie de Montpellier, Institut Charles Gerhardt Montpellier UMR 5253 CNRS, AM2N, 8 rue de l’Ecole Normale, Montpellier 34296 Cedex 5   France   Email: florian.monnier@enscm.fr   Email: marc.taillefer@enscm.fr
,
a  Ecole Nationale Supérieure de Chimie de Montpellier, Institut Charles Gerhardt Montpellier UMR 5253 CNRS, AM2N, 8 rue de l’Ecole Normale, Montpellier 34296 Cedex 5   France   Email: florian.monnier@enscm.fr   Email: marc.taillefer@enscm.fr
d  Institut Universitaire de France, IUF, 1 rue Descartes, 75231 Paris Cedex 5, France
› Author Affiliations
Further Information

Publication History

Received: 17 January 2019

Accepted: 18 January 2019

Publication Date:
13 February 2019 (online)


Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.

Supporting Information

 
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