96970-13-7Relevant academic research and scientific papers
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
Shimizu, Masaki,Nagao, Ikuhiro,Tomioka, Yosuke,Kadowaki, Tsugumi,Hiyama, Tamejiro
experimental part, p. 8014 - 8026 (2011/11/05)
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.
Palladium-catalyzed annulation of vic-bis(pinacolatoboryl)alkenes and -phenanthrenes with 2,2′-dibromobiaryls: Facile synthesis of functionalized phenanthrenes and dibenzo[g,p]chrysenes
Shimizu, Masaki,Nagao, Ikuhiro,Tomioka, Yosuke,Hiyama, Tamejiro
supporting information; experimental part, p. 8096 - 8099 (2009/04/12)
(Chemical Equation Presented) Double-cross: An annulation approach to functionalized polycyclic aromatic hydrocarbons involving a palladium-catalyzed double cross-coupling reaction of vic-diborylalkenes and -phenanthrenes with 2,2′-dibromobiaryls led to a variety of phenanthrenes and dibenzo-[g,p]chrysenes, as well as [5]helicenes, dithienobenzenes, and triphenyleno[1,2-b:4,3-b′]dithiophenes (see scheme; Bpin = pinacolatoboryl).
