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Issue 42, 2020
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Rhodium-catalyzed Sommelet–Hauser type rearrangement of α-diazoimines: synthesis of functionalized enamides

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Abstract

An efficient rhodium catalyzed Sommelet–Hauser type rearrangement of sulfur ylides derived from α-thioesters and N-sulfonyl-1,2,3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. The developed reaction involves the unprecedented [2,3]-sigmatropic rearrangement of sulfur ylides with the imine motif. Importantly, the method works well with various substituted α-thioesters/-amides/-ketones and substituted N-sulfonyl-1,2,3-triazoles and allows the synthesis of diverse enamide derivatives in good to excellent yields. The reaction was also successfully extended to the one-pot synthesis of enamides from terminal alkynes.

Graphical abstract: Rhodium-catalyzed Sommelet–Hauser type rearrangement of α-diazoimines: synthesis of functionalized enamides

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Article information


Submitted
02 Jan 2020
Accepted
08 Apr 2020
First published
08 Apr 2020

Chem. Commun., 2020,56, 5649-5652
Article type
Communication

Rhodium-catalyzed Sommelet–Hauser type rearrangement of α-diazoimines: synthesis of functionalized enamides

A. C. S. Reddy, K. Ramachandran, P. M. Reddy and P. Anbarasan, Chem. Commun., 2020, 56, 5649
DOI: 10.1039/D0CC00016G

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