Synergistic Visible Light and Pd-Catalyzed C-H Alkylation of 1-Naphthylamines with α-Diazoesters.

The combination of visible light irradiation and Pd-catalysis has been practically employed for the C-H alkylation reactions of naphthylamines and α-diazo esters, leading to the synthesis of α-naphthyl functionalized acetates via C-C bond construction under mild reaction conditions and under solvent-free conditions. The light irradiation has been proven to play a pivotal role in the reactions, probably by promoting the generation of active carbene species from α-diazo esters.

Palladium-catalyzed native α-amino acid derivative-directed arylation/oxidation of benzylic C-H bonds: synthesis of 5-aryl-1,4-benzodiazepin-2-ones.

A Pd-catalyzed, native α-amino acid derivative-directed benzylic C-H bond arylation/oxidation with aryl iodides was developed. The natural amino acid auxiliary could serve as a desired building block for formation of 5-aryl-1,4-benzodiazepin-2-ones after removal of the trifluoroacetyl protecting group. The bifunctional reaction probably proceeded through a sequential benzylic arylation/oxidation process.