Auxiliary‐Directed C(sp3)−H Arylation by Synergistic Photoredox and Palladium Catalysis. Issue 58 (21st September 2017)

• Record Type: Journal Article
• Authors: Czyz, Milena L.; Lupton, David W.; Polyzos, Anastasios
• Is Part Of: Chemistry. Volume 23:Issue 58(2017)
• Page Start: 14450
• Page End: 14453
• Publication Date: 2017-09-21
• Subjects: arylation -- C−H activation -- metallaphotoredox -- palladium -- photoredox; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201704045
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Herein we describe the auxiliary‐directed arylation of unactivated C(sp 3 )−H bonds with aryldiazonium salts, which proceeds under synergistic photoredox and palladium catalysis. The site‐selective arylation of aliphatic amides with α‐quaternary centres is achieved with high selectivity for β‐methyl C(sp 3 )−H bonds. This operationally simple method is compatible with carbocyclic amides, a range of aryldiazonium salts and proceeds at ambient conditions. Abstract : Of earth and light : An auxiliary‐directed arylation of unactivated C(sp 3 )−H bonds with synergistic photoredox and palladium catalysis is reported. This approach enables the site‐selective arylation of aliphatic amides with α‐quaternary centers and high selectivity for β‐methyl C(sp 3 )−H bonds. The operationally simple method is compatible with a range of amides, aryldiazonium salts and proceeds at room temperature.