High-yielding synthesis of Weinreb amides via homogeneous catalytic carbonylation of iodoalkenes and iodoarenes

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

“…With exception of 2-iodotiophene, no ketoamides were produced, even at higher (60 bar) CO pressure. The highest isolated yield (85%) was achieved for 1-iodo-2-methylcyclohexene (Figure 10) [52]. 2-Iodobenzyl bromide was reacted with various N-nucleophiles and the resulting 2-iodobenzylamines were aminocarbonylated in the presence of Pd complexes.…”

High-yielding synthesis of 1-isoindolinone derivatives via palladium-catalysed cycloaminocarbonylation

“…In the presence of primary amines, e.g., tert-butylamine (a), the exclusive formation of 2f can be observed (entry 2 and 4). A possible explanation for the role of the primary amine is, that instead of the carbonylation of the primary ring-closure product 6 leading to 6a and 6b, the usual carbonylation and double carbonylation of the amine (a) takes place yielding N,N 0 -di-tert-butyl-urea and N,N 0 -di-tert-butyl-glyoxylamide in a side-reaction, 26 respectively.…”

In situ generated Pd(0) nanoparticles stabilized by bis(aryl)acenaphthenequinone diimines as catalysts for aminocarbonylation reactions in water

“…18,19 Recently, the palladium-catalyzed aminocarbonylation of 5-iodoindole and 7-iodoindole derivatives with various primary and secondary amines has been reported. 20 Kollár described efficient aminocarbonylation of iodoalkenes and iodoaromatic with primary and secondary amines, catalyzed by Pd(OAc) 2 with addition of PPh 3 [21][22][23][24][25][26] . The same catalytic system has been used in aminocarbonylation of iodoalkenes and iodobenzene with diethyl α-aminobenzyl-phosphonate 27 and aminoacid methyl esters in ionic liquids.…”