Synthesis 2018; 50(02): 254-266
DOI: 10.1055/s-0036-1590957
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© Georg Thieme Verlag Stuttgart · New York

Insights into the Cobalt-Catalyzed Three-Component Coupling of Mixed Aromatic Organozinc Species, Carbonyl Compounds or Imines and Michael Acceptors: Synthetic and Mechanistic Aspects

Jérôme Paul
a  Électrochimie et Synthèse Organique, Université Paris Est, ICMPE (UMR 7182), CNRS, UPEC, F-94320 Thiais, France   Email: legall@glvt-cnrs.fr
,
Marc Presset
a  Électrochimie et Synthèse Organique, Université Paris Est, ICMPE (UMR 7182), CNRS, UPEC, F-94320 Thiais, France   Email: legall@glvt-cnrs.fr
,
a  Électrochimie et Synthèse Organique, Université Paris Est, ICMPE (UMR 7182), CNRS, UPEC, F-94320 Thiais, France   Email: legall@glvt-cnrs.fr
,
Eric Léonel
a  Électrochimie et Synthèse Organique, Université Paris Est, ICMPE (UMR 7182), CNRS, UPEC, F-94320 Thiais, France   Email: legall@glvt-cnrs.fr
,
Pascal Retailleau
b  Laboratoire de Cristallochimie, Institut de Chimie des Substances Naturelles, ICSN CNRS, Bât 27, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France
› Author Affiliations
The financial support of this work by the CNRS and Université Paris-Est (Ph.D. grant to J. P.) is gratefully acknowledged.
Further Information

Publication History

Received: 06 September 2017

Accepted after revision: 17 October 2017

Publication Date:
21 November 2017 (online)

Abstract

The first examples of cobalt-catalyzed multicomponent couplings of mixed aromatic arylzinc reagents with Michael acceptors and carbonyl compounds or imines is described. The reaction system employs a cobalt(II)-2,2′-bipyridine or a cobalt(II)-1,10-phenanthroline complex as a catalyst for both organozinc generation and subsequent multicomponent assembly by formal Michael addition/aldol coupling or Mannich reaction. This study brings new insights into the synthetic scope and mechanism of the reaction.

Supporting Information

 
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