Convenient Access to C10- and C11-(di)arylated dibenzo[ b , f ]azepines via Palladium-catalyzed C−H Bonds Cleavages

Haoran Li (1) , Thierry Roisnel (1) , Jean-François Soulé (1) , Henri Doucet (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

Conditions allowing the C10‐ and C11‐arylations of dibenzo[b,f]azepines via successive palladium‐catalyzed reactions are reported. Using aryl bromides as the aryl source, the C10‐arylation of dibenzo[b,f]azepines is very selective. Then, using benzenesulfonyl chlorides as the aryl source, the second arylation at C11‐position is achieved affording non‐symmetrical C10,C11‐diarylated dibenzo[b,f]azepines. Both reactions tolerate a variety of substituents on the aryl source.

Keywords: Palladium; Arylation; Azepines; C-C bond formation; C-H bond cleavage

Domains: Chemical Sciences

Haoran Li, Thierry Roisnel, Jean-François Soulé, Henri Doucet. Convenient Access to C10- and C11-(di)arylated dibenzo[ b , f ]azepines via Palladium-catalyzed C−H Bonds Cleavages. Advanced Synthesis and Catalysis, 2019, 361 (4), pp.791-802. ⟨10.1002/adsc.201801366⟩. ⟨hal-01988048⟩