Silver-catalyzed regioselective 1,6-hydroarylation of para-quinone methides with anilines and phenols

Biquan Xiong, Shipan Xu, Weifeng Xu, Yu Liu, Limin Zhang, Ke Wen Tang (Corresponding Author), Shuang Feng Yin (Corresponding Author), Wai Yeung Wong (Corresponding Author)

Research output: Journal article publicationJournal articleAcademic researchpeer-review

13 Citations (Scopus)

Abstract

A simple and efficient method for the silver-catalyzed regioselective 1,6-hydroarylation of para-quinone methides (p-QMs) with anilines and phenols has been established. Without the need for pre-protection, a broad range of anilines (primary amine, secondary amine and tertiary amine), phenols and para-quinone methides are well tolerated under mild conditions, giving the corresponding 1,6-hydroarylation products with moderate to good yields. Moreover, a series of modified natural products can be synthesized via this simple method. Control experiments were also performed to gain insights into the plausible reaction mechanism. This protocol has high atom economy, and may have significant implications for the formation of C(sp3)-C(sp2) bonds in organic synthesis.

Original languageEnglish
Pages (from-to)3807-3817
JournalOrganic Chemistry Frontiers
Volume9
Issue number14
DOIs
Publication statusPublished - 24 May 2022

ASJC Scopus subject areas

  • Organic Chemistry

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