Cp2ZrCl2-EtMgBr-Catalysed Reaction of 2-Zincoethylzincation of 2-Alkynylamines

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Abstract

It was found that the Cp2ZrCl2-EtMgBr-catalyzed reaction of 2-alkynylamines with Et2Zn leads to the regio- and stereoselective formation of (2Z)-allylamines in high yield. It has been established that the presence of morpholyl and piperidyl substituents in the structure of propargylamines does not interfere with the regio- and stereoselective 2-zincoethylzincation of the triple bond. Carbocyclization of α,ω-bis(aminomethyl)alkadiynes based on the Cp2ZrCl2-EtMgBr-catalyzed carbozincation reaction with Et2Zn was carried out for the first time. A mechanism for the catalytic 2-zincoethylzincation of α,ω-bis(aminomethyl)alkadiynes was proposed.

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About the authors

A. M. Gabdullin

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Author for correspondence.
Email: kadikritan@gmail.com
ORCID iD: 0000-0001-5204-7394
Russian Federation, Ufa

R. N. Kadikova

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Email: kadikritan@gmail.com
ORCID iD: 0000-0002-4636-1739
Russian Federation, Ufa

I. R. Ramazanov

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Email: kadikritan@gmail.com
ORCID iD: 0000-0002-3846-6581
Russian Federation, Ufa

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Supplementary files

Supplementary Files
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1. JATS XML
2. Scheme 1. Cp2ZrCl2-EtMgBr-catalyzed 2-zincethylzincification of substituted 2-alkynylamines with Et2Zn.

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3. Scheme 2. Proposed mechanism of catalytic 2-zincethylzincination of 2-alkynylamines.

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4. Scheme 3

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