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Issue 20, 2019
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The aryne Sommelet–Hauser rearrangement

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Abstract

An aryne induced transition-metal-free and mild Sommelet–Hauser rearrangement of tertiary benzylamines for the synthesis of α-aryl amino acid derivatives in moderate to good yields is presented. Unlike the conventional Sommelet–Hauser rearrangement of ammonium salts, the methodology developed herein requires neither harsh conditions nor strong bases. Moreover, a temperature dependent switchable selectivity for the Sommelet–Hauser and Stevens [1,2] rearrangements has been observed.

Graphical abstract: The aryne Sommelet–Hauser rearrangement

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Article information


Submitted
23 Jan 2019
Accepted
11 Feb 2019
First published
12 Feb 2019

Chem. Commun., 2019,55, 3004-3007
Article type
Communication

The aryne Sommelet–Hauser rearrangement

T. Roy, R. N. Gaykar, S. Bhattacharjee and A. T. Biju, Chem. Commun., 2019, 55, 3004
DOI: 10.1039/C9CC00629J

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