Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C-Cl site.

Autor: Chen Z; State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University Kowloon Hong Kong SAR China chau.ming.so@polyu.edu.hk., Gu C; State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University Kowloon Hong Kong SAR China chau.ming.so@polyu.edu.hk., Yuen OY; State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University Kowloon Hong Kong SAR China chau.ming.so@polyu.edu.hk., So CM; State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University Kowloon Hong Kong SAR China chau.ming.so@polyu.edu.hk.; The Hong Kong Polytechnic University Shenzhen Research Institute Shenzhen 518057 Guangdong China.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2022 Mar 16; Vol. 13 (17), pp. 4762-4769. Date of Electronic Publication: 2022 Mar 16 (Print Publication: 2022).
DOI: 10.1039/d1sc06701j
Abstrakt: This study described palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates in the Ar-Cl bond. The Pd/SelectPhos system showed excellent chemoselectivity toward the Ar-Cl bond in the presence of the Ar-OTf bond with a broad substrate scope and excellent product yields. The electronic and steric hindrance offered by the -PR 2 group of the ligand with the C2-alkyl group was found to be the key factor affecting the reactivity and chemoselectivity of the α-arylation reaction. The chemodivergent approach was also successfully employed in the synthesis of flurbiprofen and its derivatives ( e.g. , -OMe and -F).
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE