Palladium-catalyzed vinylation of aryl chlorides. Chelate effect in catalysis

Y. Ben-David, M. Portnoy, M. Gozin, David Milstein

Research output: Contribution to journalArticle

133 Citations (Scopus)

Abstract

By use of the dippb ligand (dippb = 1,4-bis-(diisopropylphosphino)butane) it is possible to effect the synthetically useful Pd-catalyzed direct vinylation of aryl chlorides; the reaction tolerates various substituents and generally results in high yields. The reaction is very sensitive to the nature of the chelating ligand, probably as a result of the need for chelate opening to allow olefin coordination and chelate closure to promote insertion. Monophosphines are ineffective. A mechanistic scheme is presented.

Original languageEnglish
Pages (from-to)1995-1996
Number of pages2
JournalOrganometallics
Volume11
Issue number6
Publication statusPublished - 1992

Fingerprint

Palladium
chelates
Catalysis
catalysis
Chlorides
palladium
chlorides
Ligands
ligands
Alkenes
butanes
Chelation
alkenes
closures
insertion
butane

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Palladium-catalyzed vinylation of aryl chlorides. Chelate effect in catalysis. / Ben-David, Y.; Portnoy, M.; Gozin, M.; Milstein, David.

In: Organometallics, Vol. 11, No. 6, 1992, p. 1995-1996.

Research output: Contribution to journalArticle

Ben-David, Y, Portnoy, M, Gozin, M & Milstein, D 1992, 'Palladium-catalyzed vinylation of aryl chlorides. Chelate effect in catalysis', Organometallics, vol. 11, no. 6, pp. 1995-1996.
Ben-David, Y. ; Portnoy, M. ; Gozin, M. ; Milstein, David. / Palladium-catalyzed vinylation of aryl chlorides. Chelate effect in catalysis. In: Organometallics. 1992 ; Vol. 11, No. 6. pp. 1995-1996.
@article{e27e813236e9410b81537932a312dd75,
title = "Palladium-catalyzed vinylation of aryl chlorides. Chelate effect in catalysis",
abstract = "By use of the dippb ligand (dippb = 1,4-bis-(diisopropylphosphino)butane) it is possible to effect the synthetically useful Pd-catalyzed direct vinylation of aryl chlorides; the reaction tolerates various substituents and generally results in high yields. The reaction is very sensitive to the nature of the chelating ligand, probably as a result of the need for chelate opening to allow olefin coordination and chelate closure to promote insertion. Monophosphines are ineffective. A mechanistic scheme is presented.",
author = "Y. Ben-David and M. Portnoy and M. Gozin and David Milstein",
year = "1992",
language = "English",
volume = "11",
pages = "1995--1996",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "6",

}

TY - JOUR

T1 - Palladium-catalyzed vinylation of aryl chlorides. Chelate effect in catalysis

AU - Ben-David, Y.

AU - Portnoy, M.

AU - Gozin, M.

AU - Milstein, David

PY - 1992

Y1 - 1992

N2 - By use of the dippb ligand (dippb = 1,4-bis-(diisopropylphosphino)butane) it is possible to effect the synthetically useful Pd-catalyzed direct vinylation of aryl chlorides; the reaction tolerates various substituents and generally results in high yields. The reaction is very sensitive to the nature of the chelating ligand, probably as a result of the need for chelate opening to allow olefin coordination and chelate closure to promote insertion. Monophosphines are ineffective. A mechanistic scheme is presented.

AB - By use of the dippb ligand (dippb = 1,4-bis-(diisopropylphosphino)butane) it is possible to effect the synthetically useful Pd-catalyzed direct vinylation of aryl chlorides; the reaction tolerates various substituents and generally results in high yields. The reaction is very sensitive to the nature of the chelating ligand, probably as a result of the need for chelate opening to allow olefin coordination and chelate closure to promote insertion. Monophosphines are ineffective. A mechanistic scheme is presented.

UR - http://www.scopus.com/inward/record.url?scp=0001104162&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001104162&partnerID=8YFLogxK

M3 - Article

VL - 11

SP - 1995

EP - 1996

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 6

ER -