Cobalt-catalyzed C–H bond functionalizations with aryl and alkyl chlorides

TitleCobalt-catalyzed C–H bond functionalizations with aryl and alkyl chlorides
Publication TypeJournal Article
Year of Publication2013
AuthorsPunji, B, Song, W, Shevchenko, GA, Ackermann, L
JournalChemistry - A European Journal
Volume19
Issue32
Pagination10605–10610
Date PublishedAUG
Abstract

Inexpensive cobalt catalysts derived from N-heterocylic carbenes (NHC) allowed efficient catalytic C[BOND]H 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 C[BOND]H 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 C[BOND]H bond acidity was found to largely govern their reactivity.

DOI10.1002/chem.201301409
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

5.48

Divison category: 
Organic Chemistry