Novel synthesis of a non-symmetric N1CN2-Pd(II) pincer complex by a tandem reaction using a meta-hydroxylated imine ligand

Alcives Avila-Sorrosa; Hugo A. Jiménez-Vázquez; Alicia Reyes-Arellano; J. Roberto Pioquinto-Mendoza; Rubén A. Toscano; Lucero González-Sebastián; David Morales-Morales

doi:10.1016/j.jorganchem.2016.06.019

Novel synthesis of a non-symmetric N¹CN²-Pd(II) pincer complex by a tandem reaction using a meta-hydroxylated imine ligand

Alcives Avila-Sorrosa, Hugo A. Jiménez-Vázquez, Alicia Reyes-Arellano, J. Roberto Pioquinto-Mendoza, Rubén A. Toscano, Lucero González-Sebastián, David Morales-Morales

Escuela Nacional de Ciencias Biológicas (ENCB)

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

The reflux reaction of ligand 3-[(2,4,6-trimethyl-phenylimino)-methyl]-phenol (1) with [Pd(NCPh)₂Cl₂] in toluene in presence of a base, results in the facile formation of the non-symmetric N¹CN²-Pd(II) pincer complex (2). The overall tandem reaction involves the benzonitrile activation at the nitrile moiety and a C-H activation process at the aromatic ring of (1) providing a pincer compound with one six and one five membered palladacycles, this structure was unequivocally confirmed by single crystal X-ray diffraction analysis. Complex (2) was used in Suzuki-Miyaura couplings demonstrating this compound to be an efficient catalyst for these transformations.

Original language	English
Pages (from-to)	69-75
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	819
DOIs	https://doi.org/10.1016/j.jorganchem.2016.06.019
State	Published - 15 Sep 2016

Keywords

Catalysis
Crystal structures
Nitrile activation
Non-symmetric pincer complexes
Palladium complexes
Schiff base compounds
Suzuki-Miyaura couplings

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10.1016/j.jorganchem.2016.06.019

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Avila-Sorrosa, A., Jiménez-Vázquez, H. A., Reyes-Arellano, A., Pioquinto-Mendoza, J. R., Toscano, R. A., González-Sebastián, L., & Morales-Morales, D. (2016). Novel synthesis of a non-symmetric N¹CN²-Pd(II) pincer complex by a tandem reaction using a meta-hydroxylated imine ligand. Journal of Organometallic Chemistry, 819, 69-75. https://doi.org/10.1016/j.jorganchem.2016.06.019

@article{928f5149eacd40618dfa128691cc4aff,

title = "Novel synthesis of a non-symmetric N1CN2-Pd(II) pincer complex by a tandem reaction using a meta-hydroxylated imine ligand",

abstract = "The reflux reaction of ligand 3-[(2,4,6-trimethyl-phenylimino)-methyl]-phenol (1) with [Pd(NCPh)2Cl2] in toluene in presence of a base, results in the facile formation of the non-symmetric N1CN2-Pd(II) pincer complex (2). The overall tandem reaction involves the benzonitrile activation at the nitrile moiety and a C-H activation process at the aromatic ring of (1) providing a pincer compound with one six and one five membered palladacycles, this structure was unequivocally confirmed by single crystal X-ray diffraction analysis. Complex (2) was used in Suzuki-Miyaura couplings demonstrating this compound to be an efficient catalyst for these transformations.",

keywords = "Catalysis, Crystal structures, Nitrile activation, Non-symmetric pincer complexes, Palladium complexes, Schiff base compounds, Suzuki-Miyaura couplings",

author = "Alcives Avila-Sorrosa and Jim{\'e}nez-V{\'a}zquez, {Hugo A.} and Alicia Reyes-Arellano and Pioquinto-Mendoza, {J. Roberto} and Toscano, {Rub{\'e}n A.} and Lucero Gonz{\'a}lez-Sebasti{\'a}n and David Morales-Morales",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier B.V.",

year = "2016",

month = sep,

day = "15",

doi = "10.1016/j.jorganchem.2016.06.019",

language = "Ingl{\'e}s",

volume = "819",

pages = "69--75",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

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Avila-Sorrosa, A , Jiménez-Vázquez, HA , Reyes-Arellano, A, Pioquinto-Mendoza, JR, Toscano, RA, González-Sebastián, L & Morales-Morales, D 2016, 'Novel synthesis of a non-symmetric N¹CN²-Pd(II) pincer complex by a tandem reaction using a meta-hydroxylated imine ligand', Journal of Organometallic Chemistry, vol. 819, pp. 69-75. https://doi.org/10.1016/j.jorganchem.2016.06.019

TY - JOUR

T1 - Novel synthesis of a non-symmetric N1CN2-Pd(II) pincer complex by a tandem reaction using a meta-hydroxylated imine ligand

AU - Avila-Sorrosa, Alcives

AU - Jiménez-Vázquez, Hugo A.

AU - Reyes-Arellano, Alicia

AU - Pioquinto-Mendoza, J. Roberto

AU - Toscano, Rubén A.

AU - González-Sebastián, Lucero

AU - Morales-Morales, David

PY - 2016/9/15

Y1 - 2016/9/15

N2 - The reflux reaction of ligand 3-[(2,4,6-trimethyl-phenylimino)-methyl]-phenol (1) with [Pd(NCPh)2Cl2] in toluene in presence of a base, results in the facile formation of the non-symmetric N1CN2-Pd(II) pincer complex (2). The overall tandem reaction involves the benzonitrile activation at the nitrile moiety and a C-H activation process at the aromatic ring of (1) providing a pincer compound with one six and one five membered palladacycles, this structure was unequivocally confirmed by single crystal X-ray diffraction analysis. Complex (2) was used in Suzuki-Miyaura couplings demonstrating this compound to be an efficient catalyst for these transformations.

AB - The reflux reaction of ligand 3-[(2,4,6-trimethyl-phenylimino)-methyl]-phenol (1) with [Pd(NCPh)2Cl2] in toluene in presence of a base, results in the facile formation of the non-symmetric N1CN2-Pd(II) pincer complex (2). The overall tandem reaction involves the benzonitrile activation at the nitrile moiety and a C-H activation process at the aromatic ring of (1) providing a pincer compound with one six and one five membered palladacycles, this structure was unequivocally confirmed by single crystal X-ray diffraction analysis. Complex (2) was used in Suzuki-Miyaura couplings demonstrating this compound to be an efficient catalyst for these transformations.

KW - Catalysis

KW - Crystal structures

KW - Nitrile activation

KW - Non-symmetric pincer complexes

KW - Palladium complexes

KW - Schiff base compounds

KW - Suzuki-Miyaura couplings

UR - http://www.scopus.com/inward/record.url?scp=84975795397&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2016.06.019

DO - 10.1016/j.jorganchem.2016.06.019

M3 - Artículo

AN - SCOPUS:84975795397

SN - 0022-328X

VL - 819

SP - 69

EP - 75

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Novel synthesis of a non-symmetric N¹CN²-Pd(II) pincer complex by a tandem reaction using a meta-hydroxylated imine ligand

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