797762-46-0

Upstream product

• 797762-38-0 N-(2-iodophenyl)-N,3-dimethylbenzamide 
• 6832-87-7 2-bromo-N-methylaniline 
• 90971-88-3 methyl 2-bromo-5-methylbenzoate 

Relevant academic research and scientific papers

A Pd-catalyzed, boron ester-mediated, reductive cross-coupling of two aryl halides to synthesize tricyclic biaryls

Tricyclic biaryls are important scaffold structures in many natural products and lead compounds in drug discovery. The formation of a biaryl unit is often the key step for the synthesis of tricyclic biaryls. Despite significant progress toward the synthesis of biaryl compounds in recent years, the direct cross-coupling of two different aryl halides is still challenging and robust methods are lacking. Herein we report a direct cross-coupling of two different aryl halides in the presence of a palladium catalyst and boron ester, which provides a new and useful complementary method to synthesize tricyclic biaryls.

Samarium(II)-mediated spirocyclization by intramolecular aryl radical addition onto an aromatic ring

(Chemical Equation Presented) Samarium(II)-mediated spirocyclization by intramolecular addition of aryl radicals onto an aromatic ring was achieved by the reaction of N-(2-iodophenyl)-N-alkylbenzamides with SmI2 in the presence of HMPA, yielding spirocyclic indolin-2-one derivatives. The ether congeners afford spirocyclic benzofuran derivatives in moderate yields by aryl radical addition onto a benzene ring without having an electron-withdrawing group. The reaction with other aryl groups such as naphthalene and indole rings is also described.

The first samarium(II)-mediated aryl radical cyclisation onto an aromatic ring

Intramolecular arylation of aryl radicals was mediated by SmI 2/HMPA in the presence of i-PrOH to give spirocycles and/or reduced cine-cyclised products, while the reaction in the absence of i-PrOH gave the rearomatised fused rings.