An enlarged imidazolinium salt with a molecular mass of nearly 800 g/mol was synthesized and the respective N-heterocyclic carbene (NHC= N, N ′-bis(2,6-diisopropyl-4-CH 2 NCy 2 -phenyl)-4,5-dihydroimidazol-2-ylidene) converted into (NHC)Pd(allyl)Cl and (NHC)Pd(cinnamyl)Cl complexes. The cinnamyl complex displays excellent activities in the Suzuki−Miyaura coupling and the Buchwald−Hartwig amination. The separation of this complex from the coupling products by means of a solvent-resistant nanofiltration using a PDMS (polydimethylsiloxane) membrane on PAN (polyacrylonitrile) was tested, and very high retention of between 97% and 99.9% of the (NHC)Pd complex was observed. The residual Pd content in the cross-coupling products is in the range 3.5−25 ppm.
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Schoeps et al. (2009) studied this question.
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