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 language | English |
|---|---|
| Pages (from-to) | 10025-10028 |
| Number of pages | 4 |
| Journal | Chemistry - A European Journal |
| Volume | 15 |
| Issue number | 39 |
| DOIs | |
| Publication status | Published - Oct 5 2009 |
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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 journal › Article
}
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
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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 -