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Issue 10, 2010
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A comparison between nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in hydroamination of activated olefins

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Abstract

A comparison is drawn between the nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in the hydroamination of activated olefins. Though all of the newly designed nickel and palladium precatalysts, trans-[1-i-propyl-4-R-1,2,4-triazol-5-ylidene]2MBr2 [R = Et, M = Ni (1b); R = Et, M = Pd (1c); R = CH2CH[double bond, length as m-dash]CH2, M = Ni (2b) and R = CH2CH[double bond, length as m-dash]CH2, M = Pd (2c)], are moderately active for hydroamination reaction of a variety of secondary amines viz. morpholine, piperidine, pyrrolidine and diethylamine with activated olefins like, acrylonitrile, methyl acrylate, ethyl acrylate and t-butyl acrylate at room temperature in 1 hour, the nickel complexes (1b and 2b) exhibited superior activity compared to its palladium counterparts (1c and 2c). The better performance of the nickel complexes has been correlated to the more electron deficient metal center in the nickel 1b and 2b complexes than in the palladium 1c and 2c analogs based on the density functional theory studies. The 1b-c and 2b-c complexes were synthesized by the reaction of 1-i-propyl-4-R-1,2,4-triazolium bromide [R = Et (1a) and R = CH2CH[double bond, length as m-dash]CH2 (2a)] with MCl2 [M = Ni, Pd] in presence of NEt3 as a base.

Graphical abstract: A comparison between nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in hydroamination of activated olefins

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Article information


Submitted
01 Sep 2009
Accepted
10 Dec 2009
First published
21 Jan 2010

Dalton Trans., 2010,39, 2515-2524
Article type
Paper

A comparison between nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in hydroamination of activated olefins

C. Dash, M. M. Shaikh, R. J. Butcher and P. Ghosh, Dalton Trans., 2010, 39, 2515
DOI: 10.1039/B917892A

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