Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 48, Pages 11669-11676Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201702283
Keywords
alkyne; annulation; cobalt; dihydroisoquinoline; picolinamide
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Funding
- Spanish Ministerio de Economia, Industria y Competitividad (MINECO), MINECO/FEDER, UE [CTQ2012-35790, CTQ2015-66954-P]
- MICINN
- European Commission [CIG: CHAAS-304085]
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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 O-2 as the sole oxidant and Co(OAc)(2) as 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 alpha-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.
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