Experimental and theoretical studies on the oxidative addition of palladium(0) to β-chlorovinamidinium salts

Ian W. Davies; Jimmy Wu; Jean François Marcoux; Mark Taylor; David Hughes; Paul J. Reider; Robert J. Deeth

doi:10.1016/S0040-4020(01)00350-7

Experimental and theoretical studies on the oxidative addition of palladium(0) to β-chlorovinamidinium salts

Ian W. Davies, Jimmy Wu, Jean François Marcoux, Mark Taylor, David Hughes, Paul J. Reider, Robert J. Deeth

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Boronic acids, esters and borinic anhydrides are partners in Suzuki-Miyaura cross-coupling reactions with a variety of β-chlorovinamidinium salts to give the desired β-arylvinamidinium salts in up to 88% yield. Reduction is a competing reaction pathway. DFT calculations on the intermediate palladium complex reveal that the Pd-C interaction is predominantly of σ-symmetry and the metal based LUMO is mainly d_z2 in character.

Original language	English (US)
Pages (from-to)	5061-5066
Number of pages	6
Journal	Tetrahedron
Volume	57
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4020(01)00350-7
State	Published - Jun 11 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)00350-7

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abstract = "Boronic acids, esters and borinic anhydrides are partners in Suzuki-Miyaura cross-coupling reactions with a variety of β-chlorovinamidinium salts to give the desired β-arylvinamidinium salts in up to 88% yield. Reduction is a competing reaction pathway. DFT calculations on the intermediate palladium complex reveal that the Pd-C interaction is predominantly of σ-symmetry and the metal based LUMO is mainly dz2 in character.",

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T1 - Experimental and theoretical studies on the oxidative addition of palladium(0) to β-chlorovinamidinium salts

AU - Davies, Ian W.

AU - Wu, Jimmy

AU - Marcoux, Jean François

AU - Taylor, Mark

AU - Hughes, David

AU - Reider, Paul J.

AU - Deeth, Robert J.

PY - 2001/6/11

Y1 - 2001/6/11

N2 - Boronic acids, esters and borinic anhydrides are partners in Suzuki-Miyaura cross-coupling reactions with a variety of β-chlorovinamidinium salts to give the desired β-arylvinamidinium salts in up to 88% yield. Reduction is a competing reaction pathway. DFT calculations on the intermediate palladium complex reveal that the Pd-C interaction is predominantly of σ-symmetry and the metal based LUMO is mainly dz2 in character.

AB - Boronic acids, esters and borinic anhydrides are partners in Suzuki-Miyaura cross-coupling reactions with a variety of β-chlorovinamidinium salts to give the desired β-arylvinamidinium salts in up to 88% yield. Reduction is a competing reaction pathway. DFT calculations on the intermediate palladium complex reveal that the Pd-C interaction is predominantly of σ-symmetry and the metal based LUMO is mainly dz2 in character.

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U2 - 10.1016/S0040-4020(01)00350-7

DO - 10.1016/S0040-4020(01)00350-7

M3 - Article

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SN - 0040-4020

VL - 57

SP - 5061

EP - 5066

JO - Tetrahedron

JF - Tetrahedron

IS - 24

ER -

Experimental and theoretical studies on the oxidative addition of palladium(0) to β-chlorovinamidinium salts

Abstract

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