The Suzuki Cross-couplings Of N’-mesyl Arylhydrazines And Of Tetrahydroquinoline Catalyzed By Lactin Via Povarov

Biaryl compounds are widely common in natural products, agrochemicals,pharmaceuticals, pesticide, and so on. Therefore, the development of new and effective procedure to synthesis of biaryls is very important. Suzuki-Miyaura cross-coupling reaction is one of the most reliable methods to get biaryl compound.N’-Tosylarylhydrazines have been used in Suzuki cross-coupling reaction as electrophilic reagents to form biaryl compound. Considering the atom economic, we used N’-mesyl arylhydrazine to instead of it. The tetrahydroquinoline skeleton is an important structural unit found in many biologically active natural products and synthetic pharmaceuticals. Tetrahydroquinoline derivatives display a broad range of biological, medicinal, and pharmacological properties, For example, bradykinin antagonists, antiallergic agents, antitumor agents, and NMDA receptor antagonists are all tetrahydroquinoline derivatives. Among the currently available synthetic methodologies, the Povarov reaction is one of the most facile and practical approaches to synthesis of tetrahydroquinolines. A series of catalysts, such as GdCl3, SmI2,lanthanide cpmplex, chiral phosphoric acid and Selectflour have been used as efficient catalysts for this reaction. In This paper, We adopted eco-friend, cheap and accessible lactin as a new catalyst..This paper has been divided into two parts. Firstly, we developed a novel C-N bond cleavage for the preparation of biaryl compouds by Pd-catalyzed Suzuki cross-coupling between N’-mesyl arylhydrazine and aryl boronic acid. With 5 mol%Pd(OAc)2 as catalyst, potassium carbonate as the base, a series of biaryl compouds has been obtained in moderate to good yields.Secondly, we described a novel methodolgy for the synthesis of tetrahydroquinoline derivatives via a three-component one-pot Povarov reaction using lactic as a safe and economical catalyst. With 0.5 eq. lactic as catalyst, the products were obtained in moderate to good yields with a wide range of substrates.