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

A. M. Gabdullin; Габдуллин А. М.; R. N. Kadikova; Кадикова Р. Н.; I. R. Ramazanov; Рамазанов И. Р.

doi:10.31857/S0514749224010056

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

Authors: Gabdullin A.M.¹, Kadikova R.N.¹, Ramazanov I.R.¹
Affiliations:
1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences
Issue: Vol 60, No 1 (2024)
Pages: 68-74
Section: Articles
URL: https://bakhtiniada.ru/0514-7492/article/view/272382
DOI: https://doi.org/10.31857/S0514749224010056
EDN: https://elibrary.ru/ENKQWW
ID: 272382

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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.

Keywords

2-alkynylamines, 2-zincoethylzincation, α,ω-bis(aminomethyl)alkadiynes, (2Z)-allylamines, zirconocene catalysis, diethylzinc

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