N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts

Addition reactions; Carboxylation; Catalysis; Organic compounds; Azolium salts; Michael additions; N-heterocyclic carbenes; Precatalysts; Carbon dioxide; Michael addition

Abstract :

[en] N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is, NHC·CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.

Disciplines :

Chemistry

Author, co-author :

Hans, Morgan ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène

Rodriguez, Jean; Aix Marseille Université, Centrale Marseille, CNRS, 13397 Marseille, France

Coquerel, Yoann; Aix Marseille Université, Centrale Marseille, CNRS, 13397 Marseille, France

Language :

English

Title :

N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts

Publication date :

2014

Journal title :

Journal of Organic Chemistry

ISSN :

0022-3263

eISSN :

1520-6904

Publisher :

American Chemical Society, Washington, United States - District of Columbia

Volume :

Issue :

Pages :

2758-2764

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 28 April 2014

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