Recyclable Silver-Catalyzed Selective Hydrogenation of Imides to Primary Amines via Dual C–N Bond Cleavage

Abstract

We report the first heterogeneous catalytic hydrogenation of N-substituted imides and polyimide to generate primary amines, diols, and lactones. Catalyzed by Ag/TiO 2 , this reaction proceeded smoothly in high yields and selectivities for N-alkyl and N-aryl phthalimides and N-aryl succinimides, which also had activity for the degradation of waste polyimide plastics. In contrast to the typical Gabriel process, this reaction does not need any toxic reagent, and the byproducts are also very useful. Recycling experiments showed that the catalyst Ag/TiO 2 could be easily recovered without a decrease in catalytic activity.

Two-step synthesis of vicinal trifluoromethyl primary amines from α-(trifluoromethyl)styrenes and phthalimide

“…9 N -Alkyl phthalimides are versatile building blocks in organic synthesis, especially for the synthesis of primary alkylamines uncontaminated by secondary or tertiary amine by-products. 10 Many elegant methodologies have been developed for the transformation of readily available phthalimides into N -substituted phthalimides (Scheme 1a–f). 11 The Gabriel reaction is one of the classical and powerful methods for the synthesis of primary amines.…”

CuI–Amidobis(phosphine)-Catalyzed Direct Amidation of Unactivated Alkanes via C(sp3)–H Activation

“…The formation of C–N bonds holds paramount significance in the synthesis of medicines, pharmaceutical molecules, and organic group functionalization. − In this context, the C–H functionalization approach offers a sustainable and atom-economical route for the synthesis of nitrogen-containing compounds. − Although direct functionalization of C–H bonds to create C–N bonds has been achieved, often, using expensive transition metal complexes, , C­(sp 3 )–H functionalization presents a notable challenge due to the low polarity and poor reactivity of these bonds. − As a result, reports on the inter- and intramolecular functionalization of unactivated C–H bonds are relatively scarce …”