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Issue 6, 2020
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Copper-catalyzed stereoselective alkylhydrazination of alkynes

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Abstract

An unprecedented Cu-catalyzed stereoselective alkylhydrazination reaction involving terminal alkynes, azocarboxylic esters as a nitrogen source, and dimethyl 2,2′-azobis(2-methylpropionate) and its analogues as a carbon source is presented here. This protocol provides direct access to tri-substituted (E)-alkenyl-hydrazines with good regio- and stereoselectivity under mild conditions. The transformation proceeds without an external oxidant or additives and shows good functional group tolerance. The alkenylhydrazine products could be easily converted into valuable 1,4-dicarbonyl and allyl carboxylic derivatives.

Graphical abstract: Copper-catalyzed stereoselective alkylhydrazination of alkynes

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Supplementary files

Article information


Submitted
12 Oct 2019
Accepted
10 Dec 2019
First published
12 Dec 2019

Chem. Commun., 2020,56, 920-923
Article type
Communication

Copper-catalyzed stereoselective alkylhydrazination of alkynes

J. Lei, H. Gao, M. Huang, X. Liu, Y. Mao and X. Xie, Chem. Commun., 2020, 56, 920
DOI: 10.1039/C9CC07998J

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