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

Abstract Titanium(IV) isopropoxide and ethylmagnesium bromide catalyzed reaction of 2-alkynylamines with Et 2 Zn, 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-...

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Bibliographic Details
Published in:Synlett 2019-02, Vol.30 (3), p.311-314
Main Authors: Kadikova, Rita N., Ramazanov, Ilfir R., Mozgovoi, Oleg S., Gabdullin, Azat M., Dzhemilev, Usein M.
Format: Article
Language:English
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Summary:Abstract Titanium(IV) isopropoxide and ethylmagnesium bromide catalyzed reaction of 2-alkynylamines with Et 2 Zn, 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 Et 2 Zn in the presence of catalytic amounts of Ti(O- i Pr) 4 and EtMgBr leads to trisubstituted 1-alkenylphosphine oxides with high regioselectivity and stereoselectivity.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1612009