2-Zincoethylzincation of 2-Alkynylamines and 1-Alkynylphosphines Catalyzed by Titanium(IV) Isopropoxide and Ethylmagnesium Bromide

Rita N. Kadikova; Ilfir R. Ramazanov; Oleg S. Mozgovoi; Azat M. Gabdullin; Usein M. Dzhemilev

doi:10.1055/s-0037-1612009

Synlett, Table of Contents

Synlett 2019; 30(03): 311-314
DOI: 10.1055/s-0037-1612009

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2-Zincoethylzincation of 2-Alkynylamines and 1-Alkynylphosphines Catalyzed by Titanium(IV) Isopropoxide and Ethylmagnesium Bromide

Authors

Rita N. Kadikova*

Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation Email: kadikritan@gmail.com
Ilfir R. Ramazanov
Oleg S. Mozgovoi
Azat M. Gabdullin
Usein M. Dzhemilev

Abstract

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Abstract

Titanium(IV) isopropoxide and ethylmagnesium bromide catalyzed reaction of 2-alkynylamines with Et₂Zn, followed by deuterolysis/hydrolysis and iodinolysis, affords substituted (Z)-pent-2-en-2,5-d ₂-1-amines, (Z)-pent-2-en-1-amines (65–88%), and substituted (Z)-2,5-diiodopent-2-en-1-amines (55–63%). It is suggested that the reaction proceeds through the formation of cyclic organotitanium derivatives. The reaction between 1-alkynylphosphines and Et₂Zn in the presence of catalytic amounts of Ti(O-iPr)₄ and EtMgBr leads to trisubstituted 1-alkenylphosphine oxides with high regioselectivity and stereoselectivity.

Key words

2-alkynylamines - 1-alkynylphosphines - 2-zincoethylzincation - titanium catalysis

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References

References and Notes
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