3-Amino-1-methyl-1 H-pyridin-2-one-Directed Pd II Catalysis: C(sp 3 )-H Activated Diverse Arylation Reaction

• Published in: Organic letters Vol. 20; no. 13; pp. 4062 - 4066
• Main Authors: Pati, Tanmay K, Debnath, Sudipto, Kundu, Mrinalkanti, Khamrai, Uttam, Maiti, Dilip K
• Format: Journal Article
• Language: English
• Published: United States 06-07-2018
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/acs.orglett.8b01618

A new bidentate directing group, 3-amino-1-methyl-1 H-pyridin-2-one, is introduced to achieve a powerful Pd
metallacycle for selective γ-C(sp
)-H activation and arylation of aromatic and aliphatic carboxylic acid derivatives. The versatility of the directing group is validated for remote arylation of β-C(sp
)-H, β-C(sp
)-H, and γ-C(sp
)-H to achieve therapeutically important 2-pyridone analogues and arylated acid synthons. The traceless removal of the directing group to retrieve the directing element and carboxylic acids makes this method more interesting.