Issue 43, 2019

An imidazolin-2-iminato ligand organozinc complex as a catalyst for hydroboration of organic nitriles

Abstract

The reaction of diethylzinc with imidazolin-2-imines (ImRNH, R = Dipp (2,6-diisopropylphenyl)), Mes (2,4,6-trimethylphenyl), and tBu (tert-butyl) afforded the corresponding dimeric zinc(II) imidazolin-2-iminato complexes [{(ImRN)Zn(CH2CH3)}2] (R = Dipp, 1a; R = Mes, 1b; R = tBu, 1c). The zinc complexes were characterised using spectroscopic techniques and the molecular structure of complex 1b was established by single-crystal X-ray diffraction analysis. Complex 1c was used as a catalyst for the chemo-selective hydroboration of organic nitriles with pinacolborane (HBpin) at ambient temperature to obtain diborylamines of a broad substrate scope in high yield. Zinc complex 1c exhibits a versatile substrate scope and good functional group tolerance for catalytic hydroboration reactions. A most plausible mechanism is proposed on the basis of the kinetic study.

Graphical abstract: An imidazolin-2-iminato ligand organozinc complex as a catalyst for hydroboration of organic nitriles

Supplementary files

Article information

Article type
Paper
Submitted
06 Aug 2019
Accepted
04 Oct 2019
First published
07 Oct 2019

New J. Chem., 2019,43, 16812-16818

An imidazolin-2-iminato ligand organozinc complex as a catalyst for hydroboration of organic nitriles

S. Das, J. Bhattacharjee and T. K. Panda, New J. Chem., 2019, 43, 16812 DOI: 10.1039/C9NJ04076E

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