1091603-71-2Relevant articles and documents
Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids
Deng, Guobo,Liang, Yun,Luo, Xiai,Yang, Xiumei,Yang, Yuan,Yang, Yuzhong,Zhou, Liwei
supporting information, p. 1223 - 1230 (2020/04/15)
A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.
Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of o-Iodobiphenyls or (Z)-β-Halostyrenes with o-Bromobenzyl Alcohols through Two Sequential C-C Bond Formations Catalyzed by a Palladium Complex
Iwasaki, Masayuki,Araki, Yasuhiro,Iino, Shohei,Nishihara, Yasushi
, p. 9247 - 9263 (2015/09/28)
o-Bromobenzyl alcohol has been developed as a novel annulating reagent, bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently coupled o-iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols to afford triphenylenes and phenanthrenes, respectively. The present cascade reaction proceeded through deacetonative cross-coupling and sequential intramolecular cyclization. An array of experimental data suggest that the reaction mechanism involves the equilibrium of 1,4-palladium migration.
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.
