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Electrooxidative para-selective C-H/N-H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives.

ABSTRACT: Oxidative C-H/N-H cross-coupling is one of the most atom-economical methods for the construction of C-N bonds. However, traditional oxidative C-H/N-H cross-coupling either required the use of strong oxidants or high reaction temperature, which makes it difficult to tolerate redox active functional groups. Herein we describe an external chemical oxidant-free electrooxidative C-H/N-H cross-coupling between electron-rich arenes and diarylamine derivatives. Under undivided electrolytic conditions, a series of triarylamine derivatives are produced from electron-rich arenes and diarylamine derivatives with high functional group tolerance. Both of the coupling partners are redox active in oxidative C-H/N-H cross-coupling, which enables high regioselectivity in C-N bond formation. Exclusive para-selectivity is observed for the coupling with anilines.

SUBMITTER: Liu K

PROVIDER: S-EPMC6367370 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Electrooxidative para-selective C-H/N-H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives.

Liu Kun K Tang Shan S Wu Ting T Wang Shengchun S Zou Minzhu M Cong Hengjiang H Lei Aiwen A

Nature communications 20190207 1

Oxidative C-H/N-H cross-coupling is one of the most atom-economical methods for the construction of C-N bonds. However, traditional oxidative C-H/N-H cross-coupling either required the use of strong oxidants or high reaction temperature, which makes it difficult to tolerate redox active functional groups. Herein we describe an external chemical oxidant-free electrooxidative C-H/N-H cross-coupling between electron-rich arenes and diarylamine derivatives. Under undivided electrolytic conditions, a ...[more]

PMID: 30733447

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