Issue 13, 2020

Recent developments in 1,6-addition reactions of para-quinone methides (p-QMs)

Abstract

In recent years, para-quinone methides (p-QMs) have emerged as attractive and versatile synthons in organic synthesis owing to their high reactivity. Consequently, p-QM chemistry has attracted increasing attention and remarkable advances have been achieved. Among the numerous transformations involving p-QMs, catalytic reactions play a pivotal role, and a variety of catalytic systems mediated by Lewis acids, Brønsted acids, bases, transition metals, N-heterocyclic carbenes, and other catalysts have been established for performing 1,6-conjugate addition reactions. Various molecular scaffolds have been constructed using p-QMs to obtain the core structures of numerous natural and synthetic substances of chemical and biomedical relevance. In this review, we provide a comprehensive overview of recent progress in this rapidly growing field by summarizing the 1,6-conjugate addition and annulation reactions of p-QMs with consideration of their mechanisms and applications.

Graphical abstract: Recent developments in 1,6-addition reactions of para-quinone methides (p-QMs)

Article information

Article type
Review Article
Submitted
30 mar 2020
Accepted
28 maj 2020
First published
28 maj 2020

Org. Chem. Front., 2020,7, 1743-1778

Recent developments in 1,6-addition reactions of para-quinone methides (p-QMs)

J. Wang, W. Hao, S. Tu and B. Jiang, Org. Chem. Front., 2020, 7, 1743 DOI: 10.1039/D0QO00387E

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