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 |
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Authors: | Masaki Shimizu Ikuhiro NagaoYosuke Tomioka Tsugumi KadowakiTamejiro Hiyama |
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Institution: | a Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan b Research and Development Initiative, Chuo University, 1-13-27, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan |
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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, dibenzog,p]chrysenes, and triphenyleno1,2-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 dibenzog,p]chrysenes in high yields. |
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Keywords: | Annulation Aromatic hydrocarbons Boron Cross-coupling reaction Palladium |
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