A coordination controlled aryl-halide oxidative addition to platinum

Olena V. Zenkina, Amir Karton, Linda J W Shimon, Jan M L Martin, Milko van der Boom

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Aryl-halide bond activation and coordination of unsaturated substrates are key steps in many metal-mediated carbon-carbon bond-forming reactions. A series of reactions with stillbenes 1-7 and Pt(PEt3)4 were used to explore the role of substrate coordination on aryl-halide activation. The complexes 8-14 were characterized by NMR spectroscopy, and complexes 9-12 and 14 were isolated and characterized by elemental analysis. Nearly identical spectroscopic properties were reported for structurally related stillbazole complexes. Prolonged reaction times and elevated temperatures resulted in the quantitative formation of complexes 15-21. The X-ray structure of complex 12, confirms the n2-coordination of the central carbon-carbon double bond of the stillbene to the metal center. A good linear correlation was observed between the rates of these transformations and the electronic properties of the substituent of the stillbenes.

Original languageEnglish
Pages (from-to)10025-10028
Number of pages4
JournalChemistry - A European Journal
Volume15
Issue number39
DOIs
Publication statusPublished - Oct 5 2009

Fingerprint

Platinum
Carbon
Metals
Chemical activation
Substrates
Electronic properties
Nuclear magnetic resonance spectroscopy
X rays
Chemical analysis
Temperature

Keywords

  • Aryl-halide activation
  • Bond activation
  • Olefin coordination
  • Platinum
  • Substituent effects

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

A coordination controlled aryl-halide oxidative addition to platinum. / Zenkina, Olena V.; Karton, Amir; Shimon, Linda J W; Martin, Jan M L; van der Boom, Milko.

In: Chemistry - A European Journal, Vol. 15, No. 39, 05.10.2009, p. 10025-10028.

Research output: Contribution to journalArticle

Zenkina, Olena V. ; Karton, Amir ; Shimon, Linda J W ; Martin, Jan M L ; van der Boom, Milko. / A coordination controlled aryl-halide oxidative addition to platinum. In: Chemistry - A European Journal. 2009 ; Vol. 15, No. 39. pp. 10025-10028.
@article{b6f9f4bcc4f843e6bf1bd2878ea9136c,
title = "A coordination controlled aryl-halide oxidative addition to platinum",
abstract = "Aryl-halide bond activation and coordination of unsaturated substrates are key steps in many metal-mediated carbon-carbon bond-forming reactions. A series of reactions with stillbenes 1-7 and Pt(PEt3)4 were used to explore the role of substrate coordination on aryl-halide activation. The complexes 8-14 were characterized by NMR spectroscopy, and complexes 9-12 and 14 were isolated and characterized by elemental analysis. Nearly identical spectroscopic properties were reported for structurally related stillbazole complexes. Prolonged reaction times and elevated temperatures resulted in the quantitative formation of complexes 15-21. The X-ray structure of complex 12, confirms the n2-coordination of the central carbon-carbon double bond of the stillbene to the metal center. A good linear correlation was observed between the rates of these transformations and the electronic properties of the substituent of the stillbenes.",
keywords = "Aryl-halide activation, Bond activation, Olefin coordination, Platinum, Substituent effects",
author = "Zenkina, {Olena V.} and Amir Karton and Shimon, {Linda J W} and Martin, {Jan M L} and {van der Boom}, Milko",
year = "2009",
month = "10",
day = "5",
doi = "10.1002/chem.200901781",
language = "English",
volume = "15",
pages = "10025--10028",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "39",

}

TY - JOUR

T1 - A coordination controlled aryl-halide oxidative addition to platinum

AU - Zenkina, Olena V.

AU - Karton, Amir

AU - Shimon, Linda J W

AU - Martin, Jan M L

AU - van der Boom, Milko

PY - 2009/10/5

Y1 - 2009/10/5

N2 - Aryl-halide bond activation and coordination of unsaturated substrates are key steps in many metal-mediated carbon-carbon bond-forming reactions. A series of reactions with stillbenes 1-7 and Pt(PEt3)4 were used to explore the role of substrate coordination on aryl-halide activation. The complexes 8-14 were characterized by NMR spectroscopy, and complexes 9-12 and 14 were isolated and characterized by elemental analysis. Nearly identical spectroscopic properties were reported for structurally related stillbazole complexes. Prolonged reaction times and elevated temperatures resulted in the quantitative formation of complexes 15-21. The X-ray structure of complex 12, confirms the n2-coordination of the central carbon-carbon double bond of the stillbene to the metal center. A good linear correlation was observed between the rates of these transformations and the electronic properties of the substituent of the stillbenes.

AB - Aryl-halide bond activation and coordination of unsaturated substrates are key steps in many metal-mediated carbon-carbon bond-forming reactions. A series of reactions with stillbenes 1-7 and Pt(PEt3)4 were used to explore the role of substrate coordination on aryl-halide activation. The complexes 8-14 were characterized by NMR spectroscopy, and complexes 9-12 and 14 were isolated and characterized by elemental analysis. Nearly identical spectroscopic properties were reported for structurally related stillbazole complexes. Prolonged reaction times and elevated temperatures resulted in the quantitative formation of complexes 15-21. The X-ray structure of complex 12, confirms the n2-coordination of the central carbon-carbon double bond of the stillbene to the metal center. A good linear correlation was observed between the rates of these transformations and the electronic properties of the substituent of the stillbenes.

KW - Aryl-halide activation

KW - Bond activation

KW - Olefin coordination

KW - Platinum

KW - Substituent effects

UR - http://www.scopus.com/inward/record.url?scp=70349693930&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70349693930&partnerID=8YFLogxK

U2 - 10.1002/chem.200901781

DO - 10.1002/chem.200901781

M3 - Article

VL - 15

SP - 10025

EP - 10028

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 39

ER -