Ortho-selective C-H arylation of phenols with N-carboxyindoles under Bronsted acid- or Cu(i)-catalysis.

ABSTRACT: Control over chemo- and regioselectivity is a critical issue in the heterobiaryl synthesis via C-H oxidative coupling. To address this challenge, a strategy to invert the normal polarity of indoles in the heterobiaryl coupling was developed. With N-carboxyindoles as umpoled indoles, an exclusively ortho-selective coupling with phenols has been realized, employing a Brønsted acid- or Cu(i)-catalyst (as low as 0.01 mol%). A range of phenols and N-carboxyindoles coupled with exceptional efficiency and selectivity at ambient temperature and the substrates bearing redox-active aryl halides (-Br and -I) smoothly coupled in an orthogonal manner. Notably, preliminary examples of atropselective heterobiaryl coupling have been demonstrated, based on a chiral disulfonimide

SUBMITTER: Nguyen NH 

PROVIDER: S-EPMC8790926 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature