Synthesis of Di-Substituted Alkynes via Palladium-Catalyzed Decarboxylative Coupling and C-H Activation

Alberto Gomez-Herrera; Fady Nahra; Jiufeng Wu; Frederic Izquierdo; Marcel Brill; Catherine S. J. Cazin; Steven P. Nolan

doi:10.1002/slct.201803805

Synthesis of Di-Substituted Alkynes via Palladium-Catalyzed Decarboxylative Coupling and C-H Activation

Alberto Gomez-Herrera, Fady Nahra, Jiufeng Wu, Frederic Izquierdo, Marcel Brill, Catherine S. J. Cazin, Steven P. Nolan

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

13 Scopus citations

Abstract

A straightforward methodology for the decarboxylative cross-coupling of aryl bromides and phenylpropiolic acid using a Pd(II)-NHC catalyst has been developed. Various aryl bromides have been successfully transformed into the corresponding di-substituted alkynes using environmentally benign conditions (weak base and ethanol as solvent). This efficient catalytic system also proved useful for the copper-free Sonogashira coupling of aryl and alkenyl bromides with various terminal alkynes. The synthetic utility of these methodologies was highlighted in the synthesis of a polyaromatic compound and various fluoroenynes.

Original language	English (US)
Pages (from-to)	5-9
Number of pages	5
Journal	ChemistrySelect
Volume	4
Issue number	1
DOIs	https://doi.org/10.1002/slct.201803805
State	Published - Jan 3 2019
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2022-06-07
Acknowledgements: The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.), Syngenta (studentship to AGH), King Saud University (SPN), the EPSRC (EP/K503162/1) and the European COST action CHAOS for support. We are also grateful to Umicore for the loan of Pd complexes and to the EPSRC National Mass Spectrometry Service Centre at Swansea University for HMRS analyses. This study was partially supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR).
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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title = "Synthesis of Di-Substituted Alkynes via Palladium-Catalyzed Decarboxylative Coupling and C-H Activation",

abstract = "A straightforward methodology for the decarboxylative cross-coupling of aryl bromides and phenylpropiolic acid using a Pd(II)-NHC catalyst has been developed. Various aryl bromides have been successfully transformed into the corresponding di-substituted alkynes using environmentally benign conditions (weak base and ethanol as solvent). This efficient catalytic system also proved useful for the copper-free Sonogashira coupling of aryl and alkenyl bromides with various terminal alkynes. The synthetic utility of these methodologies was highlighted in the synthesis of a polyaromatic compound and various fluoroenynes.",

author = "Alberto Gomez-Herrera and Fady Nahra and Jiufeng Wu and Frederic Izquierdo and Marcel Brill and Cazin, {Catherine S. J.} and Nolan, {Steven P.}",

note = "KAUST Repository Item: Exported on 2022-06-07 Acknowledgements: The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.), Syngenta (studentship to AGH), King Saud University (SPN), the EPSRC (EP/K503162/1) and the European COST action CHAOS for support. We are also grateful to Umicore for the loan of Pd complexes and to the EPSRC National Mass Spectrometry Service Centre at Swansea University for HMRS analyses. This study was partially supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR). This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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doi = "10.1002/slct.201803805",

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T1 - Synthesis of Di-Substituted Alkynes via Palladium-Catalyzed Decarboxylative Coupling and C-H Activation

AU - Gomez-Herrera, Alberto

AU - Nahra, Fady

AU - Wu, Jiufeng

AU - Izquierdo, Frederic

AU - Brill, Marcel

AU - Cazin, Catherine S. J.

AU - Nolan, Steven P.

N1 - KAUST Repository Item: Exported on 2022-06-07 Acknowledgements: The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.), Syngenta (studentship to AGH), King Saud University (SPN), the EPSRC (EP/K503162/1) and the European COST action CHAOS for support. We are also grateful to Umicore for the loan of Pd complexes and to the EPSRC National Mass Spectrometry Service Centre at Swansea University for HMRS analyses. This study was partially supported by the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR). This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2019/1/3

Y1 - 2019/1/3

N2 - A straightforward methodology for the decarboxylative cross-coupling of aryl bromides and phenylpropiolic acid using a Pd(II)-NHC catalyst has been developed. Various aryl bromides have been successfully transformed into the corresponding di-substituted alkynes using environmentally benign conditions (weak base and ethanol as solvent). This efficient catalytic system also proved useful for the copper-free Sonogashira coupling of aryl and alkenyl bromides with various terminal alkynes. The synthetic utility of these methodologies was highlighted in the synthesis of a polyaromatic compound and various fluoroenynes.

AB - A straightforward methodology for the decarboxylative cross-coupling of aryl bromides and phenylpropiolic acid using a Pd(II)-NHC catalyst has been developed. Various aryl bromides have been successfully transformed into the corresponding di-substituted alkynes using environmentally benign conditions (weak base and ethanol as solvent). This efficient catalytic system also proved useful for the copper-free Sonogashira coupling of aryl and alkenyl bromides with various terminal alkynes. The synthetic utility of these methodologies was highlighted in the synthesis of a polyaromatic compound and various fluoroenynes.

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ER -

Synthesis of Di-Substituted Alkynes via Palladium-Catalyzed Decarboxylative Coupling and C-H Activation

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