title: Palladium-Catalyzed Intramolecular Carbene Insertion into C(sp(3) )-H Bonds.
abstract: A palladium-catalyzed carbene insertion into C(sp(3) )-H bonds leading to pyrrolidines was developed. The coupling reaction can be catalyzed by both Pd(0) and Pd(II) , is regioselective, and shows a broad functional group tolerance. This reaction is the first example of palladium-catalyzed C(sp(3) )-C(sp(3) ) bond assembly starting from diazocarbonyl compounds. DFT calculations revealed that this direct C(sp(3) )-H bond functionalization reaction involves an unprecedented concerted metalation-deprotonation step.
authors.affiliation: Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028, Barcelona, Spain. dsole@ub.edu.
authors.forename: Daniel
authors.initials: D
authors.lastname: Solé
authors.affiliation: Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028, Barcelona, Spain.
authors.forename: Francesco
authors.initials: F
authors.lastname: Mariani
authors.affiliation: Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028, Barcelona, Spain.
authors.forename: M-Lluïsa
authors.initials: ML
authors.lastname: Bennasar
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad Complutense de Madrid, Ciudad Universitaria, 28040, Madrid, Spain. israel@quim.ucm.es.
authors.forename: Israel
authors.initials: I
authors.lastname: Fernández
keywords: carbene insertion; density functional calculations; diazo compounds; palladium catalysis; pyrrolidines