期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 48, 页码 15790-15798出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404705
关键词
homogeneous catalysis; N-heterocyclic carbenes; palladium; PEPPSI; sulfination
资金
- NSERC (Canada)
- Eli Lilly and Company through the Lilly Research Award Program (LRAP)
A series of new, easily activated NHC-PdII precatalysts featuring a trans-oriented morpholine ligand were prepared and evaluated for activity in carbon-sulfur cross-coupling chemistry. [(IPent) PdCl2(morpholine)] (IPent= 1,3bis(2,6-di(3-pentyl) phenyl) imidazol-2-ylidene) was identified as the most active precatalyst and was shown to effectively couple a wide variety of deactivated aryl halides with both aryl and alkyl thiols at or near ambient temperature, without the need for additives, external activators, or pre-activation steps. Mechanistic studies revealed that, in contrast to other common NHC-PdII precatalysts, these complexes are rapidly reduced to the active NHC-Pd0 species at ambient temperature in the presence of KOtBu, thus avoiding the formation of deleterious off-cycle PdII-thiolate resting states.
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