[2,3]-Sommelet-Hauser重排的研究进展

Research Progress of [2,3]-Sommelet-Hauser Rearrangement

Sommelet-Hauser重排(S-H重排)是一类基于鎓盐的[2,3]-重排反应,反应过程中能够形成独特的去芳构化中间体,同时构建新的C-C键。该重排反应于1937年由Sommelet首次发现,随后Hauser等人对该反应过程进行了深入的研究。在Sommelet-Hauser重排反应发现后的很长一段时间里,由于该反应存在较多的副反应通道、产物选择性较差,关于其的进一步研究以及应用的报道较少。近些年来,随着新反应模式的发展以及新催化体系的发现,一系列新的S-H重排反应被相继开发,展现出了优异的选择性和广阔的底物兼容性,所得的反应产物骨架丰富多样。S-H重排反应又逐渐引起科学家的重视。本文通过文献查阅,并进一步分析、归纳,对S-H反应进行了深入地探讨与研究,详细阐述了该类反应的独特机制和反应的发展情况。

Sommelet-Hauser rearrangement (S-H rearrangement) is a type of [2,3]-rearrangement reaction based on onium salts. During reaction process of Sommelet-Hauser rearrangement, a unique dearomatization intermediate can be formed and a new C-C bond can be constructed finally. The rearrangement reaction was first discovered by Sommelet in 1937, and then Hauser and coworkers conducted in-depth research to understand the insight of reaction process. Since the S-H rearrangement was first discovered, due to the existence of various side reactions and its poor product selectivity, the progress on this rearrangement reaction is limited. With the development of new reaction modes and the discovery of new catalytic systems in recent years, a series of new S-H rearrangements have been developed one after another, exhibiting excellent selectivity, broad substrate compatibility, and diverse product skeletons. The S-H rearrangement reaction has gradually attracted the attention of scientists. Through literature review and further analysis, the unique mechanism and recent advance of S-H rearrangement were discussed in this paper.