The preparation of imides via the palladium-catalyzed coupling reaction as a one-carbon elongation reaction is described. The palladium-catalyzed coupling reaction of aryl-, alkyl-, and alkenylborons with N-[methoxy(methylthio)methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers that are converted to the corresponding imides by acidic hydrolysis in high yield. The imino ethers are also useful for preparing the corresponding ester without using carbon monoxide.
methylthio)methylene]carbamate as a One--Carbon Elongation Reaction. -The coupling followed by hydrolysis offers a straightforward synthesis of a variety of unsymmetrical imide structures. -(TOMIZAWA, T.; ORIMOTO, K.; NIWA, T.; NAKADA*, M.; Org. Lett. 14 (2012) 24, 6294-6297, http://dx.doi.org/10.1021/ol303062a ; Dep. Chem. Biochem., Waseda Univ., Shinjuku, Tokyo 169, Japan; Eng.) -Mais 18-059
The palladium‐catalyzed coupling of aryl(tributyl)stannanes (II) with carbamate (I) in the presence of cuprous 2‐thiophenecarboxylate leads to imino ethers (III), which are subjected to acid hydrolysis to yield imides (IV).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.