Recently, utilizing CO as a methylation reagent to construct functional chemicals has attracted significant attention. However, the conversion of CO is still a challenge due to its inherent inertness. In this study, we have developed a catalyst-free N-methylation of amines to prepare numerous methylamines using CO as a methyl source. By utilizing 2 eq. PhSiH as the reductant, amines could undergo N-methylation under 1 atm of CO in DMF at 90 °C. Aliphatic and aromatic amines were compatible, generating the desired products in up to 95% yield.
It is important to achieve diverse functionalization of tertiary anilines due to their importance in biological molecules, pharmaceutical, functional materials, and ligands. A straightforward Pd/Cu-catalyzed oxidative C-H bond activation/N-dealkylative carbonylation of tertiary [1,1'-biphenyl]-2-anilines towards the synthesis of various biologically important phenanthridin-6(5H)-ones has been developed. A wide range of functional groups are well tolerated in this transformation. Moreover, O is utilized as the terminal oxidant to promote the oxidative carbonylation process.
The Pd/Cu-catalyzed intramolecular C–H bond aminocarbonylation utilizing imines as the amine source has been developed. This transformation provides an efficient and straightforward protocol for the synthesis of phthalimides which widely exist in natural products, pharmaceutical and functional materials. Various functional groups are tolerated and the yields are up to 99%.
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