Report

Tailored quinones support high-turnover Pd catalysts for oxidative C–H arylation with O2

See allHide authors and affiliations

Science  19 Nov 2020:
eabd1085
DOI: 10.1126/science.abd1085

You are currently viewing the abstract.

View Full Text

Log in to view the full text

Log in through your institution

Log in through your institution

Abstract

Palladium(II)-catalyzed C–H oxidation reactions could streamline the synthesis of pharmaceuticals, agrochemicals, and other complex organic molecules. Existing methods, however, commonly exhibit poor catalyst performance with high Pd loading (e.g., 10 mol %) and a need for (super)stoichiometric quantities of undesirable oxidants, such as benzoquinone and silver(I) salts. The present study probes the mechanism of a representative Pd-catalyzed oxidative C–H arylation reaction and elucidates mechanistic features that undermine catalyst performance, including substrate-consuming side reactions and sequestration of the catalyst as inactive species. Systematic tuning of the quinone co-catalyst overcomes these deleterious features. Use of 2,5-di-tert-butyl-p-benzoquinone enables efficient use of molecular oxygen as the oxidant, high reaction yields, and >1900 turnovers by the palladium catalyst.

View Full Text

Stay Connected to Science