Niobium- and zirconium-catalyzed reactions of substituted 2 alkynylamines with EtZn

The NbCl 5 -EtMgBr-catalyzed reaction of N , N -disubstituted 2-alkynylamines with Et 2 Zn followed by hydrolysis or deuterolysis affords (2 Z )-alkenylamines (reduction products of alkyne) in high yields. The reaction of N , N -disubstituted 2-alkynylamines with Et 2 Zn catalyzed by the Cp 2 ZrCl 2...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2021-01, Vol.11 (8), p.4631-4638
Main Authors: Kadikova, Rita N, Ramazanov, Ilfir R, Gabdullin, Azat M, Mozgovoj, Oleg S, Dzhemilev, Usein M
Format: Article
Language:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The NbCl 5 -EtMgBr-catalyzed reaction of N , N -disubstituted 2-alkynylamines with Et 2 Zn followed by hydrolysis or deuterolysis affords (2 Z )-alkenylamines (reduction products of alkyne) in high yields. The reaction of N , N -disubstituted 2-alkynylamines with Et 2 Zn catalyzed by the Cp 2 ZrCl 2 -EtMgBr system occurs as 2-zincoethylzincation, resulting, after deuterolysis or iodinolysis, in the regio- and stereoselective formation of the corresponding dideuterated and diiodinated 2-alkenylamine derivatives with a trisubstituted double bond. This study demonstrates the difference between the catalytic effects of NbCl 5 and Cp 2 ZrCl 2 on the pathway of reaction of tertiary 2-alkynylamines with Et 2 Zn in the presence of catalytic amounts of EtMgBr. The NbCl 5 -EtMgBr-catalyzed reaction of N , N -disubstituted 2-alkynylamines with Et 2 Zn followed by hydrolysis or deuterolysis affords (2 Z )-alkenylamines (reduction products of alkyne) in high yields.
ISSN:2046-2069
DOI:10.1039/d0ra10132j