6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki–Heck coupling

•A new diphosphine ligand DADPP, which is conveniently obtained.•DADPP has excellent properties in palladium catalyzed Heck coupling.•The highest TON of 96,000,000 was obtained with 4-bromobenzaldehyde as the substrate.•The yield of 95% was gained toward 4-nitrochlorobenzene with 0.05 mol.% [Pd(C3H5)Cl]2.

A novel and conveniently prepared diphosphine ligand 6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl] (DADPP) combined with [Pd(C3H5)Cl]2 affords an efficient catalytic system for Mizoroki–Heck cross-coupling of aryl halides with alkenes. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.

Graphical abstractThe catalytic activity of [Pd(C3H5)Cl]2/DADPP in Mizoroki–Heck reaction of alkenes with various aryl halides is presented. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.Figure optionsDownload full-size imageDownload as PowerPoint slide