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Hydroamination of isocyanates and isothiocyanates by alkaline earth metal initiators supported by a bulky iminopyrrolyl ligand

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Abstract

A series of new heteroleptic alkaline earth (Ae) metal complexes of general formula [{(Ph2CHN[double bond, length as m-dash]CH)2C4H2N}AeI(THF)3] {Ae = Ca (2), Sr (3), and Ba (4)} were synthesized via salt metathesis by reacting potassium salt of ligand 1-K [{(Ph2CHN[double bond, length as m-dash]CH)2C4H2N}K(THF)2] with anhydrous alkaline earth metal diiodides (AeI2). The homoleptic calcium and barium complexes [{(Ph2CHN[double bond, length as m-dash]CH)2C4H2N}2Ae] [Ae = Ca (5), Ba (6)] were prepared by treating metal bis-hexamethyldisilazide [Ae{N(SiMe3)2}2(THF)2] with the protic ligand 1-H [(Ph2CH–N[double bond, length as m-dash]CH)2C4H2NH] in a 1 : 2 molar ratio. Calcium complex 5 was used as an active pre-catalyst for the addition of N–H bond of arylamines across the heterocumulenes such as phenylisocyanate (PhNCO) and phenylisothiocyanate (PhNCS) under neat conditions, and up to 99% yields of the corresponding urea and thiourea derivatives were obtained.

Graphical abstract: Hydroamination of isocyanates and isothiocyanates by alkaline earth metal initiators supported by a bulky iminopyrrolyl ligand

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Supplementary files

Article information


Submitted
27 Mar 2020
Accepted
05 May 2020
First published
06 May 2020

New J. Chem., 2020, Advance Article
Article type
Paper

Hydroamination of isocyanates and isothiocyanates by alkaline earth metal initiators supported by a bulky iminopyrrolyl ligand

K. Bano, S. Anga, A. Jain, H. P. Nayek and T. K. Panda, New J. Chem., 2020, Advance Article , DOI: 10.1039/D0NJ01509A

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