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Cobalt‐Catalyzed CH Bond Functionalizations with Aryl and Alkyl Chlorides
Author(s) -
Punji Benudhar,
Song Weifeng,
Shevchenko Grigory A.,
Ackermann Lutz
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301409
Subject(s) - aryl , chemistry , catalysis , steric effects , alkyl , cobalt , reactivity (psychology) , medicinal chemistry , primary (astronomy) , organic chemistry , hydrogen bond , combinatorial chemistry , molecule , medicine , alternative medicine , physics , pathology , astronomy
Inexpensive cobalt catalysts derived from N‐heterocylic carbenes (NHC) allowed efficient catalytic CH bond arylations on heteroaryl‐substituted arenes with widely available aryl chlorides, which set the stage for the preparation of sterically hindered tri‐ ortho ‐substituted biaryls. Likewise, challenging direct alkylations with β ‐hydrogen‐containing primary and even secondary alkyl chlorides proceeded on pyridyl‐ and pyrimidyl‐substituted arenes and heteroarenes. The cobalt‐catalyzed CH bond functionalizations occurred efficiently at ambient reaction temperature with excellent levels of site‐selectivities and ample scope. Mechanistic studies highlighted that electron‐deficient aryl chlorides reacted preferentially, while the arenes kinetic CH bond acidity was found to largely govern their reactivity.