Synthesis of Di-Substituted Alkynes via Palladium-Catalyzed Decarboxylative Coupling and C-H Activation
Cazin, Catherine S. J.
Nolan, Steven P.
Permanent link to this recordhttp://hdl.handle.net/10754/678648
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AbstractA 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.
CitationGómez-Herrera, A., Nahra, F., Wu, J., Izquierdo, F., Brill, M., Cazin, C. S. J., & Nolan, S. P. (2019). Synthesis of Di-Substituted Alkynes via Palladium-Catalyzed Decarboxylative Coupling and C-H Activation. ChemistrySelect, 4(1), 5–9. doi:10.1002/slct.201803805
SponsorsThe 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).
PublisherWILEY-V C H VERLAG GMBH