Herein, we disclose the hitherto unknown cross-conjugated vinylogous annulation of π-CF-allyl Pd complexes with 4-methyl-3-trifluoroacetyl-quinolones to access phenanthridones. The CF group in the Pd-π-allyl complex is key for exclusive γ-regioselectivity and further annulation. The solvent switch orchestrates the dihydro-phenanthridones (CHCN) and hydroxy-phenanthridones (DMF) in good yields, and also showed excellent optoelectronic properties.
View Article and Find Full Text PDFHerein, we report tailored 3-trifluoroacetyl-quinolin-2(1)-ones () as carbonyl and acid surrogates in Passerini- and Ugi-type reactions for the synthesis of α-trifluoromethyl-α-hydroxy carboxamides () and α-trifluoromethyl α-amino acids () in high yields, respectively. The reaction proceeds under mild reaction conditions via an exocyclic carboximidate intermediate (). The amide group in compound acts as an acid component as well as a reversible oxygen nucleophile to facilitate the reaction.
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