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

Kun Liu, Shan Tang, Ting Wu, Shengchun Wang, Minzhu Zou, Hengjiang Cong and Aiwen Lei ()
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Kun Liu: Wuhan University
Shan Tang: Wuhan University
Ting Wu: Wuhan University
Shengchun Wang: Wuhan University
Minzhu Zou: Wuhan University
Hengjiang Cong: Wuhan University
Aiwen Lei: Wuhan University

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: 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.

Date: 2019
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-08414-8

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DOI: 10.1038/s41467-019-08414-8

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