Palladium-catalyzed synthesis of β-hydroxy compounds via a strained 6,4-palladacycle from directed C-H activation of anilines and C-O insertion of epoxides.

ABSTRACT: A palladium-catalyzed C-H activation of acetylated anilines (acetanilides, 1,1-dimethyl-3-phenylurea, 1-phenylpyrrolidin-2-one, and 1-(indolin-1-yl)ethan-1-one) with epoxides using O-coordinating directing groups was accomplished. This C-H alkylation reaction proceeds via formation of a previously unknown 6,4-palladacycle intermediate and provides rapid access to regioselectively functionalized β-hydroxy products. Notably, this catalytic system is applicable for the gram scale mono-functionalization of acetanilide in good yields. The palladium-catalyzed coupling reaction of the ortho-C(sp²) atom of O-coordinating directing groups with a C(sp³) carbon of chiral epoxides offers diverse substrate scope in good to excellent yields. In addition,

SUBMITTER: Thombal RS 

PROVIDER: S-EPMC8159402 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature