Asymmetric hydroformylation with Pt-phosphine-SnCl2 and Pt-bisphosphine-CuCl2 (or CuCl) catalytic systems

L. Kollár, J. Bakos, Imre Tóth, Bálint Heil

Research output: Contribution to journalArticle

66 Citations (Scopus)

Abstract

A study has been made of asymmetric hydroformylation of styrene with PtCl2(PPh3)2 + bisphosphine + SnCl2 (bisphosphine: BDPP = (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane or DIOP = (-)-(4R,5R)-2,2-dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolane) and PtCl2(bisphosphine) + PPh3 + SnCl2 catalysts prepared "in situ". The presence of an excess of the phosphine ligand slightly lowered the reaction rate, but the enantioselectivity of these systems is significantly higher than those involving PtCl(SnCl3)(bisphosphine) catalysts. Under mild reaction conditions 88.8% enantiomeric excess was achieved. Replacing SnCl2 in these catalysts by CuCl2 or CuCl gave a new homogeneous catalytic system which is active at higher reaction temperature (> 100°C), but has a rather moderate enantioselectivity.

Original languageEnglish
Pages (from-to)257-261
Number of pages5
JournalJournal of Organometallic Chemistry
Volume370
Issue number1-3
DOIs
Publication statusPublished - Jul 11 1989

Fingerprint

phosphine
Hydroformylation
Styrene
phosphines
Enantioselectivity
Ligands
catalysts
Catalysts
Temperature
pentanes
styrenes
Reaction rates
reaction kinetics
ligands
cupric chloride
formal glycol
2,4-bis(diphenylphosphino)pentane

ASJC Scopus subject areas

  • Biochemistry
  • Chemical Engineering (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Materials Chemistry

Cite this

Asymmetric hydroformylation with Pt-phosphine-SnCl2 and Pt-bisphosphine-CuCl2 (or CuCl) catalytic systems. / Kollár, L.; Bakos, J.; Tóth, Imre; Heil, Bálint.

In: Journal of Organometallic Chemistry, Vol. 370, No. 1-3, 11.07.1989, p. 257-261.

Research output: Contribution to journalArticle

@article{7c885f0aaf54432ea6b69d74a9a98f1c,
title = "Asymmetric hydroformylation with Pt-phosphine-SnCl2 and Pt-bisphosphine-CuCl2 (or CuCl) catalytic systems",
abstract = "A study has been made of asymmetric hydroformylation of styrene with PtCl2(PPh3)2 + bisphosphine + SnCl2 (bisphosphine: BDPP = (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane or DIOP = (-)-(4R,5R)-2,2-dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolane) and PtCl2(bisphosphine) + PPh3 + SnCl2 catalysts prepared {"}in situ{"}. The presence of an excess of the phosphine ligand slightly lowered the reaction rate, but the enantioselectivity of these systems is significantly higher than those involving PtCl(SnCl3)(bisphosphine) catalysts. Under mild reaction conditions 88.8{\%} enantiomeric excess was achieved. Replacing SnCl2 in these catalysts by CuCl2 or CuCl gave a new homogeneous catalytic system which is active at higher reaction temperature (> 100°C), but has a rather moderate enantioselectivity.",
author = "L. Koll{\'a}r and J. Bakos and Imre T{\'o}th and B{\'a}lint Heil",
year = "1989",
month = "7",
day = "11",
doi = "10.1016/0022-328X(89)87289-4",
language = "English",
volume = "370",
pages = "257--261",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",
number = "1-3",

}

TY - JOUR

T1 - Asymmetric hydroformylation with Pt-phosphine-SnCl2 and Pt-bisphosphine-CuCl2 (or CuCl) catalytic systems

AU - Kollár, L.

AU - Bakos, J.

AU - Tóth, Imre

AU - Heil, Bálint

PY - 1989/7/11

Y1 - 1989/7/11

N2 - A study has been made of asymmetric hydroformylation of styrene with PtCl2(PPh3)2 + bisphosphine + SnCl2 (bisphosphine: BDPP = (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane or DIOP = (-)-(4R,5R)-2,2-dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolane) and PtCl2(bisphosphine) + PPh3 + SnCl2 catalysts prepared "in situ". The presence of an excess of the phosphine ligand slightly lowered the reaction rate, but the enantioselectivity of these systems is significantly higher than those involving PtCl(SnCl3)(bisphosphine) catalysts. Under mild reaction conditions 88.8% enantiomeric excess was achieved. Replacing SnCl2 in these catalysts by CuCl2 or CuCl gave a new homogeneous catalytic system which is active at higher reaction temperature (> 100°C), but has a rather moderate enantioselectivity.

AB - A study has been made of asymmetric hydroformylation of styrene with PtCl2(PPh3)2 + bisphosphine + SnCl2 (bisphosphine: BDPP = (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane or DIOP = (-)-(4R,5R)-2,2-dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolane) and PtCl2(bisphosphine) + PPh3 + SnCl2 catalysts prepared "in situ". The presence of an excess of the phosphine ligand slightly lowered the reaction rate, but the enantioselectivity of these systems is significantly higher than those involving PtCl(SnCl3)(bisphosphine) catalysts. Under mild reaction conditions 88.8% enantiomeric excess was achieved. Replacing SnCl2 in these catalysts by CuCl2 or CuCl gave a new homogeneous catalytic system which is active at higher reaction temperature (> 100°C), but has a rather moderate enantioselectivity.

UR - http://www.scopus.com/inward/record.url?scp=0000600484&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000600484&partnerID=8YFLogxK

U2 - 10.1016/0022-328X(89)87289-4

DO - 10.1016/0022-328X(89)87289-4

M3 - Article

VL - 370

SP - 257

EP - 261

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 1-3

ER -