Continuous-Flow N-Heterocyclic Carbene Generation and Organocatalysis

[en] Two methods were assessed for the generation of common N heterocyclic carbenes (NHCs) from stable imidazol(in)¬ium precursors using convenient and straightforward continuous-flow setups with either a heterogeneous inorganic base (Cs2CO3 or K3PO4) or a homoge¬neous organic base (KN(SiMe3)2). In-line quenching with carbon disulfide revealed that the homogeneous strategy was most efficient for the preparation of a small library of NHCs. The generation of free nucleophilic carbenes was next telescoped with two benchmark NHC-catalyzed reactions, namely, the transesterification of vinyl acetate with benzyl alcohol and the amidation of N-Boc-glycine methyl ester with ethanolamine. Both organocatalytic transfor¬ma¬tions proceeded with total conversion and excellent yields were achieved after extraction, showcasing the first examples of continuous-flow organocatalysis with NHCs.

Disciplines :

Chemistry

Author, co-author :

Di Marco, Lorenzo; University of Liège > Department of Chemistry > Center for Integrated Technology and Organic Synthesis

Hans, Morgan; University of Liège > Department of Chemistry > Center for Integrated Technology and Organic Synthesis

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

Monbaliu, Jean-Christophe ; Université de Liège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis

Language :

English

Title :

Continuous-Flow N-Heterocyclic Carbene Generation and Organocatalysis

Publication date :

2016

Journal title :

Chemistry

ISSN :

0947-6539

eISSN :

1521-3765

Publisher :

Wiley

Volume :

Pages :

4508–4514

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 04 February 2016

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