Synlett 2019; 30(03): 311-314
DOI: 10.1055/s-0037-1612009
letter
© Georg Thieme Verlag Stuttgart · New York

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

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
› Author Affiliations
18-03-00817
This work was supported by the Russian Foundation for Basic Research (grant no. 16-33-60167, 18-03-00817) and by Grant of the RF President (Sci. Sh.-6651.2016.3).
Further Information

Publication History

Received: 07 November 2018

Accepted after revision: 18 December 2018

Publication Date:
10 January 2019 (online)


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.

Supporting Information