Rhodium-Catalyzed Carbon-Carbon Bond Formation viaCleavage of Aryl-Alkenyl Bonds

摘要

Metal-catalyzed bond formation via cleavage of unstrained C-C single bonds has attractedincreasing attention since such strategies would provide unconventional methods to synthesizecomplex organic molecules.Although there have been a large number of reports on unstrainedC-C bond functionalization,types of cleavable C-C bonds are still limited.Especially,C-Cbonds next to polar groups such as cyano,carbonyl,imino and hydroxyl groups have been oftentargeted as the cleavage sites.In contrast,catalytic functionalization of nonpolar C-C bondsis relatively unexplored.Recently,our group reported a rhodium-catalyzed direct alkenylationof allylbenzenes via C-C bond cleavage,which is considered to occur byhydrometalation/chelation-assisted β-carbon elimination.We then envisioned thattransformation of C(aryl)-C(alkenyl) bond would also take place using the hydrometalation/β-carbon elimination strategy,and the metalacyclic intermediate formed after C-C bond cleavagewould be used for various C-C bond forming reactions.