Transformation of tert‐Butyl Amide Directing Groups to Nitriles in Iridium‐Catalyzed C−H Bond Functionalizations

Abstract

To overcome limitations of the directing group in IrCp* catalysis for CÀ H functionalization, we developed a directing group transformation strategy that was applied after obtaining the desired products. Well-established Ircatalyzed alkenylation, alkylation, and arylation reactions were performed under mild conditions, and then the stable coordinating amide groups were efficiently converted to versatile nitrile groups by in situ treatment with Vilsmeier reagent at room temperature. Whereas the conversion of primary amides has been extensively studied with modified Appel protocol, nitrile formation from secondary amides is very limited. Various ortho-functionalized benzonitrile derivatives (31 examples) were synthesized using this simple methodology, and the subsequent oxidative cyclization of an ortho-alkenylated product was investigated to demonstrate the synthetic utility of this strategy. This simple and versatile methodology should be available under various transition metal catalysis with stable amide directing groups.

From Biotechnology to Bioeconomy: A Review of Development Dynamics and Pathways

“…The development of South Korea's bioeconomy is driven by biotechnology like that of Germany, but the difference lies in the fact that South Korea's biotechnology R & D is mainly organized and implemented by the government. Its biotechnology promotion policy began in 1982, when the Ministry of Science and Technology took biotechnology as the core strategic technology and then formulated the Genetic Engineering Promotion Law (now the Biotechnology Promotion Law) to provide a legal basis for promoting the development of biotechnology [56].…”