199190-41-5Relevant articles and documents
Synthesis of amides by palladium-catalyzed decarbonylative coupling of carboxylic acids with isocyanides
Huang, Lin,Guo, Haili,Pan, Lingxia,Xie, Chunsong
, p. 6027 - 6031 (2013)
Amides were synthesized from carboxylic acids and isocyanides under Pd II/AgI/base catalytic conditions. The reaction conditions were optimized, and the scope was studied. Various carboxylic acids and aryl isocyanides are compatible with this reaction, but alkyl isocyanides are not. A plausible mechanism, which features distinctive PdII-mediated decarbonylative coupling and unprecedented nucleophilic attack of carboxylates to PdII-ligated isocyanides, was proposed to account for this reaction. N-Arylamides are assembled in high yields from carboxylic acids and isocyanides under PdII/AgI/base catalytic conditions. The decarbonylative coupling features unprecedented nucleophilic attack of the carboxylate on the isocyanide, which acts as an electrophile as a result of its coordination to PdII, and this inverted reactivity is proposed to account for this transformation.