Suzuki coupling catalyzed by chloro({2-[mesityl(quinolin-8-yl-kappa N)boryl]-3,5-dimethylphenyl}methyl-kappa C)palladium(II)

Sem Raj Tamang; Andreas J. Achazi; Haley S. Rust; Pramod Dhungana; Pere Miro; James D. Hoefelmeyer

doi:10.1016/j.tet.2019.03.001

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Suzuki coupling catalyzed by chloro({2-[mesityl(quinolin-8-yl-kappa N)boryl]-3,5-dimethylphenyl}methyl-kappa C)palladium(II)

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Suzuki coupling catalyzed by chloro({2-[mesityl(quinolin-8-yl-kappa N)boryl]-3,5-dimethylphenyl}methyl-kappa C)palladium(II)

Sem Raj Tamang, Andreas J. Achazi, Haley S. Rust, Pramod Dhungana, Pere Miro and James D. Hoefelmeyer

Tetrahedron, Vol.75(16), pp.2365-2370

04/19/2019

DOI: 10.1016/j.tet.2019.03.001

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Abstract

The title compound was evaluated as catalyst for Suzuki coupling of aryl halides (X = I, Br) with phenylboronic acid at room temperature. The rates of the reactions increase with increasing Hammet sigma constant of m-substituents on the arylhalide. The presence of ortho groups on the arylhalides had the effect of lowering the reaction rates. Density functional theory study of the mechanism for the formation of a Pd-(0) complex from the title molecule was performed. Reductive elimination of chloride and the eta(4)-BCCC moiety was endergonic and ruled out as a likely pathway. Instead, conversion of the title molecule to phenyl({2-[mesityl(quinolin-8-yl-kappa N)boryl]-3,5-dimethylphenyl}methyl-kappa C)palladium(II) complex is thermodynamically favored and predicted to further react with the solvent and the Suzuki coupling reagents to undergo reductive elimination of diphenyl to form a reactive Pd-(0) complex. (C) 2019 Elsevier Ltd. All rights reserved.

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Title: Subtitle: Suzuki coupling catalyzed by chloro({2-[mesityl(quinolin-8-yl-kappa N)boryl]-3,5-dimethylphenyl}methyl-kappa C)palladium(II)
Creators: Sem Raj Tamang - University of South Dakota
Andreas J. Achazi - University of South Dakota
Haley S. Rust - University of South Dakota
Pramod Dhungana - University of South Dakota
Pere Miro - University of South Dakota
James D. Hoefelmeyer - University of South Dakota
Resource Type: Journal article
Publication Details: Tetrahedron, Vol.75(16), pp.2365-2370
DOI: 10.1016/j.tet.2019.03.001
ISSN: 0040-4020
eISSN: 1464-5416
Publisher: Elsevier
Number of pages: 6
Grant note: South Dakota Board of Regents EPS-0554609; CHE-1229035; EPS-0903804; DGE-0903685; CHE-1757652 / National Science Foundation; National Science Foundation (NSF) ACI-1626516 / NSF; National Science Foundation (NSF) South Dakota Governor's Office of Economic Development through the Center for Fluorinated Functional Materials
Language: English
Date published: 04/19/2019
Academic Unit: Chemistry
Record Identifier: 9984618647302771

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