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Publication 52  

  1. Direct Access to Furoindolines by Palladium-Catalyzed Intermolecular Carboamination
    Vincent Bizet, Gustavo M. Borrajo-Calleja, Celine Besnard, Clément Mazet*
    ACS Catal. 2016, 6, 7183-7187
    [ Highlighted in: Synfacts 2016, 1257 ]

A versatile Pd-catalyzed intermolecular syn-carboamination of dihydrofurans giving access to the ubiquitous furoindoline motif is described. The efficiency of the process relies on the use of Buchwald-type biarylphosphines and the perfect control for site-selectivity of Pd insertion across the C=C bond. A catalytic sequence consisting of Heck and carboamination cross-coupling reactions from readily available dihydrofurans affords - in usually high chemical yields and highlevels of diastereocontrol - poly(hetero)cyclic compounds that would be difficult to access by established methods. Encouraging preliminary results for the enantioselective carboamination of 2,3-dihydrofurans are also disclosed.

open archive unige:89512

Editor’s version DOI: 10.1021/acscatal.6b02238