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

Organic Chemistry Frontiers Pub Date: 2022-05-24 DOI: 10.1039/D2QO00541G

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.

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