1091603-71-2Relevant academic research and scientific papers
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.
Phenanthrene Synthesis by Palladium-Catalyzed Benzannulation with o-Bromobenzyl Alcohols through Multiple Carbon-Carbon Bond Formations
Iwasaki, Masayuki,Araki, Yasuhiro,Nishihara, Yasushi
, p. 6242 - 6258 (2017/06/23)
A palladium-catalyzed benzannulation with o-bromobenzyl alcohols enabled the facile construction of phenanthrene skeletons via the sequential multiple carbon-carbon bond formations. A variety of multisubstituted phenanthrenes were synthesized by the reaction of (Z)-β-halostyrenes with o-bromobenzyl alcohols as well as by the three-component coupling of alkynes, aryl bromides, and o-bromobenzyl alcohols. The electron-deficient phosphine ligand played an important role to control the sequential oxidative addition of two different organic halides employed, which realized the selective formation of the desired phenanthrenes in good yields. This synthetic protocol was also applicable to the synthesis of the highly fused polycyclic aromatic hydrocarbons such as tetraphenes.
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.
KOt-Bu/DMF promoted intramolecular cyclization of 1,1′-biphenyl aldehydes and ketones: An efficient synthesis of phenanthrenes
Chen, Yan-Yan,Zhang, Niu-Niu,Ye, Lin-Miao,Chen, Jia-Hua,Sun, Xiang,Zhang, Xue-Jing,Yan, Ming
, p. 48046 - 48049 (2015/06/16)
A new synthesis of phenanthrene derivatives has been achieved through intramolecular cyclization of 1,1′-biphenyl aldehydes and ketones promoted by KOt-Bu/DMF. A free radical reaction pathway is proposed.
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).
