Protic and substituted NCN palladium(II) pincer complexes with 1,3-bis(benzimidazol-2′-yl)-2-bromobenzenes: Structure and catalysis

Protic and substituted NCN palladium(II) pincer complexes with... A new class of sparingly soluble NCN palladium(II) pincer complexes of the type (NˆCˆN)PdBr: [Methyl(NˆCˆN)PdBr], C26H25N4PdBr (14), [Tosyl(NˆCˆN)PdBr], C38H33N4O4S2PdBr (15), [Benzyl(NˆCˆN)PdBr], C38H33N4PdBr (16) and [Pentyl(NˆCˆN)PdBr], C34H41N4PdBr (17) [(NˆCˆN) = 5-tert-butyl-1,3-bis-(N-substituted-benzimidazol-2′-yl)phenyl] were synthesized by the treatment of palladium(0) precursor, Pd2(dba)3 with 5-tert-butyl-1,3-bis-(N-substituted-benzimidazol-2′-yl)-2-bromobenzenes (10–13) via oxidative addition with chemical yield of 46–70%. Complex 15 decomposed in [D6]DMSO to yield the protic palladacycle 18, [H(NˆCˆN)PdBr], C24H21N4PdBr, which was confirmed by the time-dependent 1H NMR studies, IR spectroscopy, mass spectrometry and the structure was corroborated with X-ray crystallographic studies. Complexes 14–18 are the fully characterized examples of NCN palladium(II) pincer complexes incorporating the N-substituted-5-tert-butyl-1,3-bis-(benzimidazol-2′-yl)-2-bromobenzene framework. The palladium(II) pincer complexes have been studied for C-H functionalization of benzyl nitriles with N-tosylaldimines to form β-aminonitriles. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Organometallic Chemistry Elsevier

Protic and substituted NCN palladium(II) pincer complexes with 1,3-bis(benzimidazol-2′-yl)-2-bromobenzenes: Structure and catalysis

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Publisher
Elsevier
Copyright
Copyright © 2018 Elsevier B.V.
ISSN
0022-328X
eISSN
1872-8561
D.O.I.
10.1016/j.jorganchem.2018.01.027
Publisher site
See Article on Publisher Site

Abstract

A new class of sparingly soluble NCN palladium(II) pincer complexes of the type (NˆCˆN)PdBr: [Methyl(NˆCˆN)PdBr], C26H25N4PdBr (14), [Tosyl(NˆCˆN)PdBr], C38H33N4O4S2PdBr (15), [Benzyl(NˆCˆN)PdBr], C38H33N4PdBr (16) and [Pentyl(NˆCˆN)PdBr], C34H41N4PdBr (17) [(NˆCˆN) = 5-tert-butyl-1,3-bis-(N-substituted-benzimidazol-2′-yl)phenyl] were synthesized by the treatment of palladium(0) precursor, Pd2(dba)3 with 5-tert-butyl-1,3-bis-(N-substituted-benzimidazol-2′-yl)-2-bromobenzenes (10–13) via oxidative addition with chemical yield of 46–70%. Complex 15 decomposed in [D6]DMSO to yield the protic palladacycle 18, [H(NˆCˆN)PdBr], C24H21N4PdBr, which was confirmed by the time-dependent 1H NMR studies, IR spectroscopy, mass spectrometry and the structure was corroborated with X-ray crystallographic studies. Complexes 14–18 are the fully characterized examples of NCN palladium(II) pincer complexes incorporating the N-substituted-5-tert-butyl-1,3-bis-(benzimidazol-2′-yl)-2-bromobenzene framework. The palladium(II) pincer complexes have been studied for C-H functionalization of benzyl nitriles with N-tosylaldimines to form β-aminonitriles.

Journal

Journal of Organometallic ChemistryElsevier

Published: Mar 15, 2018

References

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