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Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis.

ABSTRACT: The direct, catalytic arylation of simple arenes in small excess with aryl bromides is disclosed. The developed method does not require the assistance of directing groups and relies on a synergistic catalytic cycle in which phosphine-ligated silver complexes cleave the aryl C-H bond, while palladium catalysts enable the formation of the biaryl products. Mechanistic experiments, including kinetic isotope effects, competition experiments, and hydrogen-deuterium exchange, support a catalytic cycle in which cleavage of the C-H bond by silver is the rate-determining step.

SUBMITTER: Tlahuext-Aca A

PROVIDER: S-EPMC8594911 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis.

Tlahuext-Aca Adrian A Lee Sarah Yunmi SY Sakamoto Shu S Hartwig John F JF

ACS catalysis 20210114 3

The direct, catalytic arylation of simple arenes in small excess with aryl bromides is disclosed. The developed method does not require the assistance of directing groups and relies on a synergistic catalytic cycle in which phosphine-ligated silver complexes cleave the aryl C-H bond, while palladium catalysts enable the formation of the biaryl products. Mechanistic experiments, including kinetic isotope effects, competition experiments, and hydrogen-deuterium exchange, support a catalytic cycle ...[more]

PMID: 34790433

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