Platinum complexes of P,N- and P,N,P-ligands and their application in the hydroformylation of styrene

Péter Pongrácz, Ioannis D. Kostas, L. Kollár

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Neutral complexes of the formula PtCl2(L) (where L = ortho-diphenylphosphino-N-(2-hydroxyethyl)-N-methylaniline (1), ortho-diphenylphosphino-N-2-(diphenylphoshinoxy)-ethyl)-N-methylaniline (2) and N,N-bis(2-(diphenylphoshinoxy)ethyl)aniline (3)) were prepared. Various binding modes, such as P,N- and P,P-bidentate and monodentate coordinations were observed with these hemilabile ligands in the parent complexes and in the triphenylphosphine-added systems. 31P NMR studies on the 'in situ' systems revealed the hemilabile character of the ligands. The platinum complexes proved to be precursors to catalysts of low activity for the hydroformylation of styrene in platinum-ligand (1, 2 or 3)-tin(II) chloride system. High chemoselectivities (up to 82%) were obtained, while the two aldehyde regioisomers were formed in almost equimolar ratio with the slight preference of the branched aldehyde, 2-phenylpropanal. Remarkable increase in regioselectivity was observed in the presence of para-toluenesulfonic acid additive using platinum-ligand (1) systems.

Original languageEnglish
Pages (from-to)149-153
Number of pages5
JournalJournal of Organometallic Chemistry
Volume723
DOIs
Publication statusPublished - Jan 1 2013

Fingerprint

Hydroformylation
Styrene
Platinum
styrenes
platinum
Ligands
ligands
Aldehydes
aldehydes
Regioselectivity
Tin
Aniline
aniline
Chlorides
tin
chlorides
Nuclear magnetic resonance
catalysts
nuclear magnetic resonance
acids

Keywords

  • Hemilabile ligands
  • Hydroformylation
  • NMR
  • P,N-ligands
  • Platinum

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Biochemistry

Cite this

Platinum complexes of P,N- and P,N,P-ligands and their application in the hydroformylation of styrene. / Pongrácz, Péter; Kostas, Ioannis D.; Kollár, L.

In: Journal of Organometallic Chemistry, Vol. 723, 01.01.2013, p. 149-153.

Research output: Contribution to journalArticle

@article{d72fda11f6284b3a97b789bdfe2d931f,
title = "Platinum complexes of P,N- and P,N,P-ligands and their application in the hydroformylation of styrene",
abstract = "Neutral complexes of the formula PtCl2(L) (where L = ortho-diphenylphosphino-N-(2-hydroxyethyl)-N-methylaniline (1), ortho-diphenylphosphino-N-2-(diphenylphoshinoxy)-ethyl)-N-methylaniline (2) and N,N-bis(2-(diphenylphoshinoxy)ethyl)aniline (3)) were prepared. Various binding modes, such as P,N- and P,P-bidentate and monodentate coordinations were observed with these hemilabile ligands in the parent complexes and in the triphenylphosphine-added systems. 31P NMR studies on the 'in situ' systems revealed the hemilabile character of the ligands. The platinum complexes proved to be precursors to catalysts of low activity for the hydroformylation of styrene in platinum-ligand (1, 2 or 3)-tin(II) chloride system. High chemoselectivities (up to 82{\%}) were obtained, while the two aldehyde regioisomers were formed in almost equimolar ratio with the slight preference of the branched aldehyde, 2-phenylpropanal. Remarkable increase in regioselectivity was observed in the presence of para-toluenesulfonic acid additive using platinum-ligand (1) systems.",
keywords = "Hemilabile ligands, Hydroformylation, NMR, P,N-ligands, Platinum",
author = "P{\'e}ter Pongr{\'a}cz and Kostas, {Ioannis D.} and L. Koll{\'a}r",
year = "2013",
month = "1",
day = "1",
doi = "10.1016/j.jorganchem.2012.10.018",
language = "English",
volume = "723",
pages = "149--153",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

TY - JOUR

T1 - Platinum complexes of P,N- and P,N,P-ligands and their application in the hydroformylation of styrene

AU - Pongrácz, Péter

AU - Kostas, Ioannis D.

AU - Kollár, L.

PY - 2013/1/1

Y1 - 2013/1/1

N2 - Neutral complexes of the formula PtCl2(L) (where L = ortho-diphenylphosphino-N-(2-hydroxyethyl)-N-methylaniline (1), ortho-diphenylphosphino-N-2-(diphenylphoshinoxy)-ethyl)-N-methylaniline (2) and N,N-bis(2-(diphenylphoshinoxy)ethyl)aniline (3)) were prepared. Various binding modes, such as P,N- and P,P-bidentate and monodentate coordinations were observed with these hemilabile ligands in the parent complexes and in the triphenylphosphine-added systems. 31P NMR studies on the 'in situ' systems revealed the hemilabile character of the ligands. The platinum complexes proved to be precursors to catalysts of low activity for the hydroformylation of styrene in platinum-ligand (1, 2 or 3)-tin(II) chloride system. High chemoselectivities (up to 82%) were obtained, while the two aldehyde regioisomers were formed in almost equimolar ratio with the slight preference of the branched aldehyde, 2-phenylpropanal. Remarkable increase in regioselectivity was observed in the presence of para-toluenesulfonic acid additive using platinum-ligand (1) systems.

AB - Neutral complexes of the formula PtCl2(L) (where L = ortho-diphenylphosphino-N-(2-hydroxyethyl)-N-methylaniline (1), ortho-diphenylphosphino-N-2-(diphenylphoshinoxy)-ethyl)-N-methylaniline (2) and N,N-bis(2-(diphenylphoshinoxy)ethyl)aniline (3)) were prepared. Various binding modes, such as P,N- and P,P-bidentate and monodentate coordinations were observed with these hemilabile ligands in the parent complexes and in the triphenylphosphine-added systems. 31P NMR studies on the 'in situ' systems revealed the hemilabile character of the ligands. The platinum complexes proved to be precursors to catalysts of low activity for the hydroformylation of styrene in platinum-ligand (1, 2 or 3)-tin(II) chloride system. High chemoselectivities (up to 82%) were obtained, while the two aldehyde regioisomers were formed in almost equimolar ratio with the slight preference of the branched aldehyde, 2-phenylpropanal. Remarkable increase in regioselectivity was observed in the presence of para-toluenesulfonic acid additive using platinum-ligand (1) systems.

KW - Hemilabile ligands

KW - Hydroformylation

KW - NMR

KW - P,N-ligands

KW - Platinum

UR - http://www.scopus.com/inward/record.url?scp=84868520003&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84868520003&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2012.10.018

DO - 10.1016/j.jorganchem.2012.10.018

M3 - Article

VL - 723

SP - 149

EP - 153

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -