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Pd–PEPPSI N-Heterocyclic Carbene Complexes from Caffeine: Application in Suzuki, Heck, and Sonogashira Reactions
Autorzy
Rok wydania
2022
Czasopismo
Numer woluminu
41
Strony
2281-2290
DOI
10.1021/acs.organomet.2c00262
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The first synthesis of Pd–PEPPSI N-heterocyclic carbene complexes derived from the abundant and renewable natural product caffeine is reported. The catalysts bearing 3-chloro-pyridine, pyridine, and N-methylimidazole ancillary ligands were readily prepared from the corresponding N9-Me caffeine imidazolium salt by direct deprotonation and coordination to PdX2 in the presence of N-heterocycles or by ligand displacement of PdX2(Het)2. The model Pd–PEPPSI–caffeine complex has been characterized by X-ray crystallography. The complexes were successfully employed in the Suzuki cross-coupling of aryl bromides, Suzuki cross-coupling of amides, Heck cross-coupling, and Sonogashira cross-coupling. Computational studies were employed to determine frontier molecular orbitals and bond order analysis of caffeine-derived Pd–PEPPSI complexes. This class of catalysts offers an entry to utilize benign and sustainable biomass-derived xanthine NHC ligands in the popular Pd–PEPPSI systems in organic synthesis and catalysis.
Adres publiczny
http://dx.doi.org/10.1021/acs.organomet.2c00262
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