Abstract
AbstractThe Sommelet–Hauser rearrangement of X-benzylic onium ylides (X = heteroatom) is an interesting transformation in organic synthesis. This rearrangement proceeds via dearomative [2,3]-sigmatropic rearrangement, followed by aromatization to form a carbon(sp2)–carbon(sp3) bond. Few advances were made in studies performed around 2000 on this rearrangement because of several competitive side reactions and structural limitations. However, studies performed in the last 15 years on the rearrangement have remarkably expanded the substrate scope and synthetic applications. In this review, the utility of the Sommelet–Hauser rearrangement and recent advances for the generation of onium ylides are described.1 Introduction2 Base-Induced Rearrangement3 Transition-Metal-Catalyzed Rearrangement4 Light-Mediated Rearrangement5 Aryne-Induced Rearrangement6 Conclusions and Outlook
Funder
Japan Society for the Promotion of Science
Mitsubishi Chemical Corporation
Asahi Glass Foundation
Union Tool Scholarship Foundation
Uchida Energy Science Promotion Foundation
Subject
Organic Chemistry,Catalysis
Cited by
2 articles.
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