Iron- and cobalt-catalyzed arylation of azetidines, pyrrolidines, and piperidines with Grignard reagents

Baptiste Barré; Laurine Gonnard; Rémy Campagne; Sébastien Reymond; Julien Marin; Paola Ciapetti; Marie Brellier; Amandine Guérinot; Janine Cossy

doi:10.1021/ol503043r

Iron- and cobalt-catalyzed arylation of azetidines, pyrrolidines, and piperidines with Grignard reagents

Org Lett. 2014 Dec 5;16(23):6160-3. doi: 10.1021/ol503043r. Epub 2014 Nov 17.

Authors

Baptiste Barré¹, Laurine Gonnard¹, Rémy Campagne¹, Sébastien Reymond¹, Julien Marin², Paola Ciapetti², Marie Brellier², Amandine Guérinot¹, Janine Cossy¹

Affiliations

¹ †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI ParisTech, CNRS, PSL Research University, 10, Rue Vauquelin 75231 Paris Cedex 05, France.
² ‡NovAliX, BioParc, 850 Bld Sébastien Brant, BP 30170, F-67405 Illkirch, Cedex, France.

PMID: 25401684
DOI: 10.1021/ol503043r

Abstract

Iron- and cobalt-catalyzed cross-couplings between iodo-azetidines, -pyrrolidines, -piperidines, and Grignard reagents are disclosed. The reaction is efficient, cheap, chemoselective and tolerates a large variety of (hetero)aryl Grignard reagents.

MeSH terms

Azetidines / chemistry*
Catalysis
Cobalt / chemistry*
Combinatorial Chemistry Techniques
Indicators and Reagents
Iron / chemistry*
Molecular Structure
Piperidines / chemistry*
Pyrrolidines / chemistry*

Substances

Azetidines
Indicators and Reagents
Piperidines
Pyrrolidines
Cobalt
Iron