Alkyl-methyl/ethyl Derivatives from N-(Acyloxyalkyl)phthalimides and AlMe3/AlEt3

Cobalt-Catalyzed Decarboxylative Methylation and Ethylation of Aliphatic N-(Acyloxy)phthalimides with Organoaluminum Reagents: Z.-Z. Wang, G.-Z. Wang, B. Zhao, R. Shang, Y. Fu
Synlett 2020, 31, DOI: 10.1055/s-0040-1707946


Incorporation of alkyl groups – such as methyl and ethyl – into aliphatic chains via formation of new C(sp3)–C(sp3) bonds using organometallic reagents is a straightforward and attractive, but often operationally challenging strategy in organic synthesis. A novel approach to this synthetic problem has been recently proposed by the group of Dr. Rui Shang and Professor Yao Fu from the University of Science and Technology of China (Hefei, P. R. of China), using organoaluminum compounds and aliphatic N-(acyloxy)phthalimides as reaction partners, leading to the corresponding alkyl-Me/Et derivatives.


Dr. Shang said: “The cobalt-catalyzed decarboxylative methylation reaction of aliphatic carboxylate redox-active ester with the mild reagent trimethylaluminum enables facile transformation of a carboxylate group into a methyl group, which is of importance in pharmaceutical industry, and also provides a new example of using organoaluminum reagents in decarboxylative carbon–carbon coupling methodologies.”

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