Platinum Stilbazoles: Ring-Walking Coupled with Aryl-Halide Bond Activation

D. Strawser; Amir Karton; O.V. Zenkina; M.A. Iron; L.J.W. Shimon; J.M.L. Martin; M.E. Van Der Boom

doi:10.1021/ja050613h

Platinum Stilbazoles: Ring-Walking Coupled with Aryl-Halide Bond Activation

D. Strawser, Amir Karton, O.V. Zenkina, M.A. Iron, L.J.W. Shimon, J.M.L. Martin, M.E. Van Der Boom

School of Molecular Sciences

Research output: Contribution to journal › Article

51 Citations (Scopus)

Abstract

The reaction between tetrakis(triethylphosphine)platinum(0) and 4-[trans-2-(4-bromophenyl)vinyl]pyridine (1) is examined. Initially, the metal center coordinates to the bridging double bond of 1. Complexes 2 and 3 were fully characterized, and their X-ray crystallography structures are presented. Upon heating, either in solution or in the solid state, complex 2 undergoes C−Br oxidative addition to give complex 3. Kinetic studies revealed that this conversion is unimolecular and does not involve dissociation of the metal center from the double bond. Density functional studies show that a plausible mechanism involves the metal center “walking” around the π-system from the bridging C==C double bond to the C-Br bond

Original language	English
Pages (from-to)	9322-9323
Journal	Journal of the Amercian Chemical Society
Volume	127
Issue number	26
Early online date	10 Jun 2005
DOIs	https://doi.org/10.1021/ja050613h
Publication status	Published - 6 Jul 2005

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10.1021/ja050613h

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title = "Platinum Stilbazoles: Ring-Walking Coupled with Aryl-Halide Bond Activation",

abstract = "The reaction between tetrakis(triethylphosphine)platinum(0) and 4-[trans-2-(4-bromophenyl)vinyl]pyridine (1) is examined. Initially, the metal center coordinates to the bridging double bond of 1. Complexes 2 and 3 were fully characterized, and their X-ray crystallography structures are presented. Upon heating, either in solution or in the solid state, complex 2 undergoes C−Br oxidative addition to give complex 3. Kinetic studies revealed that this conversion is unimolecular and does not involve dissociation of the metal center from the double bond. Density functional studies show that a plausible mechanism involves the metal center “walking” around the π-system from the bridging C==C double bond to the C-Br bond",

author = "D. Strawser and Amir Karton and O.V. Zenkina and M.A. Iron and L.J.W. Shimon and J.M.L. Martin and {Van Der Boom}, M.E.",

year = "2005",

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doi = "10.1021/ja050613h",

language = "English",

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T1 - Platinum Stilbazoles: Ring-Walking Coupled with Aryl-Halide Bond Activation

AU - Strawser, D.

AU - Karton, Amir

AU - Zenkina, O.V.

AU - Iron, M.A.

AU - Shimon, L.J.W.

AU - Martin, J.M.L.

AU - Van Der Boom, M.E.

PY - 2005/7/6

Y1 - 2005/7/6

N2 - The reaction between tetrakis(triethylphosphine)platinum(0) and 4-[trans-2-(4-bromophenyl)vinyl]pyridine (1) is examined. Initially, the metal center coordinates to the bridging double bond of 1. Complexes 2 and 3 were fully characterized, and their X-ray crystallography structures are presented. Upon heating, either in solution or in the solid state, complex 2 undergoes C−Br oxidative addition to give complex 3. Kinetic studies revealed that this conversion is unimolecular and does not involve dissociation of the metal center from the double bond. Density functional studies show that a plausible mechanism involves the metal center “walking” around the π-system from the bridging C==C double bond to the C-Br bond

AB - The reaction between tetrakis(triethylphosphine)platinum(0) and 4-[trans-2-(4-bromophenyl)vinyl]pyridine (1) is examined. Initially, the metal center coordinates to the bridging double bond of 1. Complexes 2 and 3 were fully characterized, and their X-ray crystallography structures are presented. Upon heating, either in solution or in the solid state, complex 2 undergoes C−Br oxidative addition to give complex 3. Kinetic studies revealed that this conversion is unimolecular and does not involve dissociation of the metal center from the double bond. Density functional studies show that a plausible mechanism involves the metal center “walking” around the π-system from the bridging C==C double bond to the C-Br bond

U2 - 10.1021/ja050613h

DO - 10.1021/ja050613h

M3 - Article

C2 - 15984831

VL - 127

SP - 9322

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JO - Journal of the Amercian Chemical Society

JF - Journal of the Amercian Chemical Society

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