Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 40, Pages 12361-12365Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604956
Keywords
cobalt catalysts; C-H activation; heterocyclization; metal intermediates
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Funding
- CSIR [02 (0242)/15/EMR-II]
- DST [EMR/2015/ 002047]
- DST
- IIT-B
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The reactivity of allenes in transition-metal-catalyzed C-H activation chemistry is governed by the formation of either alkenyl-metal (M-alkenyl) or metal-pi-allyl intermediates. Although either protonation or a beta-hydride elimination is feasible with a M-alkenyl intermediate, cyclization has remained unexplored to date. Furthermore, due to the increased steric hindrance, the regioselectivity for the intramolecular cyclization of the metal-pi-allyl intermediate was hampered towards the more substituted side. To address these issues, a unified approach to synthesize a diverse array of biologically and pharmaceutically relevant heterocyclic moieties by cobalt-catalyzed directed C-H functionalization was envisioned. Upon successful implementation, the present strategy led to the regioselective formation of dihydroisoquinolin- 1(2H)-ones, isoquinolin-1(2H)-ones, dihydropyridones, and pyridones.
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