355012-41-8Relevant academic research and scientific papers
Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates
Stang, Peter J.,Yao, Yisen,Zhang, Minghao,Zhao, Wanxiang
supporting information, p. 20090 - 20098 (2020/09/02)
The synthesis of a new tetraborylethylene (TBE) is reported, and its application in the preparation of [4+0]-tetraarylethenes (TAEs) is elucidated. TAEs have widespread applications in material science and supramolecular chemistry due to their aggregation-induced emission (AIE) properties. The divergent and stereoselective synthesis of [3+1]-, [2+2]-, and [2+1+1]-TAEs via multiple couplings of vinylboronates with aryl bromides is demonstrated. These couplings feature a broad substrate scope and excellent functional group compatibility due to mild reaction conditions. Facile access to various tetraarylethenes is provided. This strategy represents an important complement to the conventional methods employed for the synthesis of TAEs, and would be a valuable tool for synthesizing TAE-based molecules useful in functional materials, biological imaging and chemical sensing.
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).
