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Sonogashira Cross-Coupling of Aryl Ammonium Salts by Selective C–N Activation Catalyzed by Air- and Moisture-Stable, Highly Active [Pd(NHC)(3-CF3-An)Cl2] (An = Aniline) Precatalysts
Autorzy
Rok wydania
2022
Czasopismo
Numer woluminu
24
Strony
6310-6315
DOI
10.1021/acs.orglett.2c02534
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
We report the Sonogashira cross-coupling of aryl ammonium salts catalyzed by air- and moisture-stable [Pd(NHC)(3-CF3-An)Cl2] (An = aniline). This highly active Pd(II)–NHC complex features broad scope and excellent C–N activation selectivity in the challenging alkynylative cross-coupling of aryl ammonium salts. Full structural characterization and computational studies demonstrate the effect of pyridine to aniline replacement as highly effective stabilizing ancillary ligand in well-defined Pd(II)–NHCs. Considering the high reactivity and the recent commercialization of [Pd(NHC)(3-CF3-An)Cl2] (Millipore Sigma, no. 915165), this catalyst represents an attractive approach to the activation of C–N bonds of broad synthetic interest.
Słowa kluczowe
Catalysts, Cations, Cross coupling reaction, Hydrocarbons, Salts
Adres publiczny
http://dx.doi.org/10.1021/acs.orglett.2c02534
Strona internetowa wydawcy
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