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Cobalt‐Catalyzed sp 2 ‐C−H Activation: Intermolecular Heterocyclization with Allenes at Room Temperature
Author(s) -
Thrimurtulu Neetipalli,
Dey Arnab,
Maiti Debabrata,
Volla Chandra M. R.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201604956
Subject(s) - regioselectivity , chemistry , steric effects , intramolecular force , catalysis , protonation , cobalt , hydride , medicinal chemistry , intermolecular force , reactivity (psychology) , metal , combinatorial chemistry , photochemistry , stereochemistry , organic chemistry , molecule , medicine , ion , alternative medicine , pathology
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–π‐allyl intermediates. Although either protonation or a β‐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–π‐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(2 H )‐ones, isoquinolin‐1(2 H )‐ones, dihydropyridones, and pyridones.