Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes
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Two new and efficient dual catalytic procedures for the synthesis of tri- and tetra-substituted alkenes using aryl bromides and chlorides are reported. The formation of these vinyl arenes occurs independently in a one-pot relay and a one-pot cooperative procedure using well-defined Pd-NHC and Cu-NHC complexes. Mechanistic studies were performed to elucidate the key role of the solvent in each procedure as well as the formation of the key intermediate, [Cu(alkenylboron)(NHC)], allowing the transmetallation with the Pd-NHC co-catalyst in the cooperative catalysis.
Lesieur , M , Bidal , Y D , Lazreg , F , Nahra , F & Cazin , C S J 2015 , ' Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes ' ChemCatChem , vol 7 , no. 14 , pp. 2108–2112 . DOI: 10.1002/cctc.201500268R1
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Lesieur, M., Bidal, Y. D., Lazreg, F., Nahra, F. and Cazin, C. S. J. (2015), Versatile Relay and Cooperative Palladium(0) N-Heterocyclic Carbene/Copper(I) N-Heterocyclic Carbene Catalysis for the Synthesis of Tri- and Tetrasubstituted Alkenes. ChemCatChem, 7: 2108–2112, which has been published in final form at https://dx.doi.org/10.1002/cctc.201500268
The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC) for financial support. We also thank the EPSCR National Mass Spectrometry Service Centre in Swansea for the High Resolution Mass Spectrometry and Umicore for the generous gift of palladium starting materials.
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