The Directed Iron-catalyzed Cross-coupling Of Arene C-H With Alkenylaluminum Reagent

Notable achievements have been made in recent years in transition metal-catalyzed C-H activation which is one of the most important areas in organic synthesis.Providing a highly efficient and concise strategy for C-C formation.In the reaction of C-H bond with organometallic reagent has the characteristics of which can react under mild conditions,high yield and good selectivity,so it has potential application value.This paper mainly reported using inexpensive iron complexes as catalyst,introducing 8-aminoquinoline as directing group.The cross-coupling of alkenyl aluminium reagents with aryl C?sp²?-H was achieved.Different parameters were tested to screen the appropriate reaction conditions such as catalyst,ligand,oxidant.Finally,the optimum reaction conditions were determined as follows:Fe?acac?₃ as catalyst,dppen as ligand,DCB as oxidant and DMF as solvent.The selectivity of the reaction was improved in the presence of the directing groups.Subsequently,the scope of substrates was examined.This strategy is more compatible with aromatic ring attached to an acyl group,whether it containing an electron-rich or electron deficient substituent,affording the expected alkenylated products in moderate to good yields.Aromatic ring with ortha or meta-substituents gave higher yields compared to those of the corresponding no-substituents and para-substituents.The reaction takes place under mild conditions,providing a new method to form C-C bond.