Cobalt‐Catalyzed CH Bond Functionalizations with Aryl and Alkyl Chlorides. Issue 32 (2nd July 2013)

• Record Type: Journal Article
• Authors: Punji, Benudhar; Song, Weifeng; Shevchenko, Grigory A.; Ackermann, Lutz
• Is Part Of: Chemistry. Volume 19:Issue 32(2013)
• Page Start: 10605
• Page End: 10610
• Publication Date: 2013-07-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201301409
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Inexpensive cobalt catalysts derived from N‐heterocylic carbenes (NHC) allowed efficient catalytic CH bond arylations on heteroaryl‐substituted arenes with widely available aryl chlorides, which set the stage for the preparation of sterically hindered tri‐<italic>ortho</italic>‐substituted biaryls. Likewise, challenging direct alkylations with <italic>β</italic>‐hydrogen‐containing primary and even secondary alkyl chlorides proceeded on pyridyl‐ and pyrimidyl‐substituted arenes and heteroarenes. The cobalt‐catalyzed C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H bond acidity was found to largely govern their reactivity.</p> </abstract>