ChemInform Abstract: Palladium‐Catalyzed Double Cross‐Coupling Reaction of 1,2‐Bis(pinacolatoboryl)alkenes and ‐arenes with 2,2′‐Dibromobiaryls: Annulative Approach to Functionalized Polycyclic Aromatic Hydrocarbons.

Abstract

Abstract This study demonstrates that the double cross-coupling reaction of 1,2-bis(pinacolatoboryl)alkenes and -arenes with 2,2′-dibromobiaryls proceeds smoothly with the aid of a catalytic amount of Pd(PPh3)4 in the presence of excess base to give a variety of polycyclic aromatic hydrocarbons, such as phenanthrenes, [5]helicene, dithienobenzenes, triphenylenes, dibenzo[g,p]chrysenes, and triphenyleno[1,2-b:4,3-b′]dithiophenes in good to high yields. It is noteworthy that the annulations using 2,2′-dibromooctafluorobiphenyl as an electrophile furnish the otherwise difficult to synthesize octafluorophenanthrenes and semi-fluorinated dibenzo[g,p]chrysenes in high yields.