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

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.",

author = "Davies, \{Ian W.\} and Jimmy Wu and Marcoux, \{Jean Fran{\c c}ois\} and Mark Taylor and David Hughes and Reider, \{Paul J.\} and Deeth, \{Robert J.\}",

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doi = "10.1016/S0040-4020(01)00350-7",

language = "English (US)",

volume = "57",

pages = "5061--5066",

journal = "Tetrahedron",

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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.

UR - https://www.scopus.com/pages/publications/0035844686

UR - https://www.scopus.com/pages/publications/0035844686#tab=citedBy

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

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

M3 - Article

AN - SCOPUS:0035844686

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

All Science Journal Classification (ASJC) codes

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