Expanded scope of heterocyclic biaryl synthesis via a palladium-catalysed thermal decarboxylative cross-coupling reaction

Marie Kissane; Orla A. McNamara; David Mitchell; David M. Coppert; Humphrey A. Moynihan; Kurt T. Lorenz; Anita R. Maguire

doi:10.1016/j.tetlet.2011.11.051

Expanded scope of heterocyclic biaryl synthesis via a palladium-catalysed thermal decarboxylative cross-coupling reaction

Marie Kissane
, Orla A. McNamara
, David Mitchell
, David M. Coppert
, Humphrey A. Moynihan
, Kurt T. Lorenz
, Anita R. Maguire

Eli Lilly
Eli Lilly SA

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

Abstract

The palladium-catalysed decarboxylative cross-coupling of heterocyclic aromatic carboxylates and aryl halides is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and tetrabutylammonium bromide (TBAB). Utilizing a mixed solvent system consisting of N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP), the cross-coupling system operated at temperatures ranging from 80 to 140 °C.

Original language	English
Pages (from-to)	403-405
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2011.11.051
Publication status	Published - 25 Jan 2012

Keywords

Aryl halides
Biaryls
Cross-coupling
Heterocycles
Palladium

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10.1016/j.tetlet.2011.11.051

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title = "Expanded scope of heterocyclic biaryl synthesis via a palladium-catalysed thermal decarboxylative cross-coupling reaction",

abstract = "The palladium-catalysed decarboxylative cross-coupling of heterocyclic aromatic carboxylates and aryl halides is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and tetrabutylammonium bromide (TBAB). Utilizing a mixed solvent system consisting of N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP), the cross-coupling system operated at temperatures ranging from 80 to 140 °C.",

keywords = "Aryl halides, Biaryls, Cross-coupling, Heterocycles, Palladium",

author = "Marie Kissane and McNamara, \{Orla A.\} and David Mitchell and Coppert, \{David M.\} and Moynihan, \{Humphrey A.\} and Lorenz, \{Kurt T.\} and Maguire, \{Anita R.\}",

year = "2012",

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day = "25",

doi = "10.1016/j.tetlet.2011.11.051",

language = "English",

volume = "53",

pages = "403--405",

journal = "Tetrahedron Letters",

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T1 - Expanded scope of heterocyclic biaryl synthesis via a palladium-catalysed thermal decarboxylative cross-coupling reaction

AU - Kissane, Marie

AU - McNamara, Orla A.

AU - Mitchell, David

AU - Coppert, David M.

AU - Moynihan, Humphrey A.

AU - Lorenz, Kurt T.

AU - Maguire, Anita R.

PY - 2012/1/25

Y1 - 2012/1/25

N2 - The palladium-catalysed decarboxylative cross-coupling of heterocyclic aromatic carboxylates and aryl halides is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and tetrabutylammonium bromide (TBAB). Utilizing a mixed solvent system consisting of N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP), the cross-coupling system operated at temperatures ranging from 80 to 140 °C.

AB - The palladium-catalysed decarboxylative cross-coupling of heterocyclic aromatic carboxylates and aryl halides is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and tetrabutylammonium bromide (TBAB). Utilizing a mixed solvent system consisting of N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP), the cross-coupling system operated at temperatures ranging from 80 to 140 °C.

KW - Aryl halides

KW - Biaryls

KW - Cross-coupling

KW - Heterocycles

KW - Palladium

UR - https://www.scopus.com/pages/publications/84155163073

U2 - 10.1016/j.tetlet.2011.11.051

DO - 10.1016/j.tetlet.2011.11.051

M3 - Article

AN - SCOPUS:84155163073

SN - 0040-4039

VL - 53

SP - 403

EP - 405

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

Expanded scope of heterocyclic biaryl synthesis via a palladium-catalysed thermal decarboxylative cross-coupling reaction

Abstract

Keywords

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