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Published on: November 9, 2019
Rh(II)-catalyzed Sommelet-Hauser rearrangement
Mingyi Liao1, Lingling Peng, Jianbo Wang
1Beijing National Laboratory of Molecular Sciences, College of Chemistry, Peking University, Beijing 100871, China.
A new Rhodium(II)-catalyzed Sommelet-Hauser rearrangement reaction is presented. This method efficiently synthesizes ortho-substituted arylacetates using readily available starting materials.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- The Sommelet-Hauser rearrangement is a valuable transformation for synthesizing substituted aromatic compounds.
- Developing efficient and selective catalytic methods for this rearrangement remains an active area of research.
Purpose of the Study:
- To report a novel Rhodium(II)-catalyzed catalytic Sommelet-Hauser rearrangement.
- To establish an efficient synthetic route for ortho-substituted arylacetates.
Main Methods:
- The reaction involves the Rh(II)-catalyzed cyclization of aryldiazoacetates with ethyl benzylthioacetate.
- Optimization of reaction conditions to achieve high yields and selectivity.
Main Results:
- The catalytic Sommelet-Hauser rearrangement proceeds in good to excellent yields.
- The reaction demonstrates reliability and efficiency in synthesizing the target products.
Conclusions:
- A new Rh(II)-catalyzed protocol for the Sommelet-Hauser rearrangement has been successfully developed.
- This methodology offers an effective approach for the ortho-functionalization of arylacetates.
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