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Cobalt-Catalyzed ortho-C−H functionalization/alkyne annulation of benzylamine derivatives: Access to dihydroisoquinolines
Metadatos
Title:Cobalt-Catalyzed ortho-C−H functionalization/alkyne annulation of benzylamine derivatives: Access to dihydroisoquinolines
Author:Martínez, Ángel Manu; Rodríguez, Nuria; Gómez-Arrayás, Ramón; Carretero, Juan C.
Entity:UAM. Departamento de Química Orgánica
UAM Author:Carretero Gonzálvez, Juan Carlos
Publisher:Wiley
Date:2017-01-01
Citation:
10.1002/chem.201702283
Chemistry – A European Journal 23.48 (2017): 11669 - 11676
ISSN:0947-6539 (print); 1521-3765 (online)
DOI:10.1002/chem.201702283
Funded by:We thank the Spanish Ministerio de Economía, Industriay Competitividad (MINECO,Grants CTQ2012-35790andCTQ2015-66954-P,MINECO/FEDER,UE) for financial support.N.R. thanks the MICINN for a Ramón y Cajal contract and the European Commission for a Marie Curie Career Integration Grant (CIG:CHAAS-304085)
Project:Gobierno de España. CTQ2012-35790; Gobierno de España. CTQ2015-66954-P
A practical picolinamide-directed C−H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2as the sole oxidant and Co(OAc)2as precatalyst. The method is compatible with both internal and terminal alkynes and shows high versatility and functional-group tolerance. Furthermore, full preservation of enantiopurity is observed when using non-racemic α-substituted benzylamine derivatives. Kinetic analysis of the reagents and catalyst, labeling experiments, and the isolation and identification of catalytically competent Co-complexes revealed important insights about the mechanism