1. C2-Alkylation and Alkenylation of Indoles Catalyzed by a Low-Valent Cobalt Complex in the Absence of Reductant
- Author
-
Corinne Aubert, Etienne Derat, Muriel Amatore, Marc Petit, Alejandro Perez-Luna, Brendan J. Fallon, Franck Ferreira, Fabrice Chemla, Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Hétéroéléments et Coordination (DCPH), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CNRS, MRES, UPMC, ANR [ANR-12-BS07-0031-01COCACLIGHT], and CarBioRed [ANR-12-BS07-0024]
- Subjects
inorganic chemicals ,010405 organic chemistry ,Reducing agent ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Organic Chemistry ,Intermolecular force ,chemistry.chemical_element ,Alkylation ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Combinatorial chemistry ,0104 chemical sciences ,Catalysis ,Deuterium ,chemistry ,Intramolecular force ,Organic chemistry ,Density functional theory ,Physical and Theoretical Chemistry ,Cobalt - Abstract
International audience; Herein an extremely versatile, well-defined, low-valent cobalt catalyst [Co(PMe3)(4)] capable of intermolecular and intramolecular imine-directed C2-alkylation and alkenylation of indoles is reported. The reaction proceeds in the absence of reducing agents or additives, affording a range of substituted indoles and dihydropyrroloindoles in high yields and regioselectivities. With the aid of deuterium labeling studies and DFT (Density Functional Theory) calculations, a mechanism is proposed that is based on a Ligand-to-Ligand Hydrogen Transfer pathway.
- Published
- 2016