Copper-Catalyzed Claisen Rearrangement with AIBN and Allylic Alcohols

A novel and succinct method for the synthesis of N-cyanomethyl amides from allylic alcohols with AIBN as the nitrile source is developed. Owing to the coordination effect with the copper catalyst, a ketenimine intermediate is formed via couplings of isobutyronitrile radicals. The copper-activated ketenimine could subsequently be intercepted by allylic alcohols and undergo Claisen rearrangement to furnish N-cyanomethyl amides. Further functional group transformations of the N-cyanomethyl amide products are also described

Palladium-Catalyzed Dehydrogenative Difunctionalization of Aminoalkenes with Aminals as Oxidants and Electrophiles

A novel palladium-catalyzed aminomethylamination of aminoalkenes with an aminal, functioning not only as an aminomethylation reagent but also as an oxidant, was developed. This direct and operationally simple protocol provides a fundamentally novel and unique approach toward the synthesis of 2-(2-aminoethyl)­indoles and 2-(2-aminoethyl)­pyrrolidines, which are important building blocks in synthetic organic chemistry. The unity of this method was highlighted by the rapid synthesis of Alosetron, a drug used for the treatment of irritable bowel syndrome

Palladium-Catalyzed Dehydrogenative Difunctionalization of Aminoalkenes with Aminals as Oxidants and Electrophiles

A novel palladium-catalyzed aminomethylamination of aminoalkenes with an aminal, functioning not only as an aminomethylation reagent but also as an oxidant, was developed. This direct and operationally simple protocol provides a fundamentally novel and unique approach toward the synthesis of 2-(2-aminoethyl)­indoles and 2-(2-aminoethyl)­pyrrolidines, which are important building blocks in synthetic organic chemistry. The unity of this method was highlighted by the rapid synthesis of Alosetron, a drug used for the treatment of irritable bowel syndrome

Palladium-Catalyzed Dehydrogenative Difunctionalization of Aminoalkenes with Aminals as Oxidants and Electrophiles

A novel palladium-catalyzed aminomethylamination of aminoalkenes with an aminal, functioning not only as an aminomethylation reagent but also as an oxidant, was developed. This direct and operationally simple protocol provides a fundamentally novel and unique approach toward the synthesis of 2-(2-aminoethyl)­indoles and 2-(2-aminoethyl)­pyrrolidines, which are important building blocks in synthetic organic chemistry. The unity of this method was highlighted by the rapid synthesis of Alosetron, a drug used for the treatment of irritable bowel syndrome