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 journalArticlepeer-review

10 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 languageEnglish (US)
Pages (from-to)5-9
Number of pages5
JournalChemistrySelect
Volume4
Issue number1
DOIs
StatePublished - Jan 3 2019
Externally publishedYes

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.

Fingerprint

Dive into the research topics of 'Synthesis of Di-Substituted Alkynes via Palladium-Catalyzed Decarboxylative Coupling and C-H Activation'. Together they form a unique fingerprint.

Cite this