1145987-33-2Relevant articles and documents
Gold-catalyzed formation of C-O and C-C bonds: An efficient domino reaction synthesis of functionalized furans
Guo, Pengfeng
, p. 58 - 60 (2015)
An efficient gold-catalyzed domino reaction for the synthesis of furan derivatives from haloalkynes has been described. This transformation has provided a new route for the formation of C-O and C-C bonds that prepare functionalized furans.
Preparing method of 2,5-diaryl furan compound
-
Paragraph 0147-0151, (2019/10/01)
The invention belongs to the technical field of organic synthesis, and discloses a preparing method of a 2,5-diaryl furan compound. The preparing method comprises the steps that ArB(OH)2, alkali, a stabilizer and a catalyst are added into an organic solvent to obtain a reaction solution, oxygen is introduced, and heating is conducted for a reaction to obtain a 5-aryl furan-2-methanol derivative; then the 5-aryl furan-2-methanol derivative and tetrabutylammonium fluoride are added into a solvent, and stirring at the indoor temperature is conducted to obtain 5-aryl furan-2-methanol; ArB(OH)2, alkali, a stabilizer and a catalyst are added into an organic solvent to obtain a reaction solution, oxygen is introduced, and heating is conducted for a reaction to obtain the 2,5-diaryl furan compound. According to the preparing method, only furan-2,5-diyldimethanol is taken as a raw material, and the preparing method has the advantages of continuous production and low cost; meanwhile, rigid anhydrous conditions and high-temperature and high-pressure operation are not needed, and the operation is simple.
Palladium-Catalyzed Cross-Coupling of Furfuryl Alcohols with Arylboronic Acids via Aromatization-Driven Carbon?Carbon Bond Cleavage to Synthesize 5-Arylfurfuryl Alcohols and 2,5-Diaryl Furans
Huang, Guanghao,Yin, Biaolin
supporting information, p. 5576 - 5586 (2019/11/14)
Herein we report a protocol for novel palladium-catalyzed cross-coupling reactions of sustainably produced primary furfuryl alcohols with arylboronic acids to deliver 5-arylfurfuryl alcohols and 2,5-diaryl furans. Hammett plot analysis suggested that the reaction mechanism involved aromatization-driven cleavage of the carbon?carbon bond of a furan oxonium ion intermediate. This protocol provides a simple, practical way to transform 5-hydroxymethylfurfural into useful compounds. (Figure presented.).
Copper-catalyzed direct synthesis of furans and thiophenes via decarboxylative coupling of alkynyl carboxylic acids with H2O or Na2S
Irudayanathan, Francis Mariaraj,Edwin Raja, Gabriel Charles,Lee, Sunwoo
, p. 4418 - 4425 (2015/06/08)
2,5-Diaryl-substituted furans were synthesized from the copper-catalyzed decarboxylative coupling of aryl-substituted aryl propiolic acids in the presence of H2O. The homocoupling of alkynyl carboxylic acids provided 1,4-diaryldiynes, which then reacted with H2O to give the desired furans through cyclization. Addition of the copper catalyst was critical, and the addition of a ligand increased the yield of products in both the homocoupling and cyclization reactions. In addition, thiophenes could be obtained when the reaction was conducted in the presence of Na2S.
A general approach to arylated furans, pyrroles, and thiophenes
Zheng, Qingwei,Hua, Ruimao,Jiang, Jianhua,Zhang, Lei
, p. 8252 - 8256 (2015/03/05)
A general and practical synthetic method for aryl-substituted five-membered heterocycles has been developed. In the presence of KOH (30%), 1,4-diaryl-1,3-butadiynes undergo the cyclocondensation reaction with water, primary amines, and Na2S·9H2O in DMSO at 80 °C to afford 2,5-diarylfurans, 1,2,5-trisubstituted pyrroles, and 2,5-diarylthiophenes in good to high yields. Further studies have disclosed that aryl-substituted five-membered heterocycles can be also synthesized by a one-pot, two-step strategy from the terminal alkynes in DMSO firstly catalyzed by CuCl, and then via addition of KOH to promote the cyclocondensation of 1,3-butadiynes generated in situ.
Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira-Glaser cyclization sequence
Klukas, Fabian,Grunwald, Alexander,Menschel, Franziska,Mueller, Thomas J. J.
, p. 672 - 679 (2014/04/17)
2,5-Di(hetero)arylfurans are readily accessible in a pseudo five-component reaction via a Sonogashira-Glaser coupling sequence followed by a superbase-mediated (KOH/DMSO) cyclization in a consecutive one-pot fashion. Besides the straightforward synthesis of natural products and biologically active molecules all representatives are particularly interesting due to their bright blue luminescence with remarkably high quantum yields. The electronic structure of the title compounds is additionally studied with DFT computations.
Mono- and biscouplings using triarylbismuths for the atom-efficient arylations of functionalized furans under palladium catalysis
Rao, Maddali L. N.,Awasthi, Dheeraj K.,Talode, Jalindar B.
supporting information; experimental part, p. 1907 - 1912 (2012/09/22)
Palladium-catalyzed cross-coupling reactions of functionalized bromofurans with triarylbismuths have been described for the atom-economic synthesis of functionalized arylfuran systems. The coupling reactions using triarylbismuths with various 2-bromofurans and 2,5-dibromofuran underwent smoothly to afford the corresponding 2-arylfurans and 2,5-diarylfurans in high yields in a short reaction time (one hour). Georg Thieme Verlag Stuttgart · New York.
Copper(I)-catalyzed synthesis of 2,5-disubstituted furans and thiophenes from haloalkynes or 1,3-diynes
Jiang, Huanfeng,Zeng, Wei,Li, Yibiao,Wu, Wanqing,Huang, Liangbing,Fu, Wei
experimental part, p. 5179 - 5183 (2012/07/03)
A regioselective synthesis of 2,5-disubstituted furans using copper(I) catalyst from haloalkynes in a one-pot procedure has been reported. This chemistry proceeds through the hydration reaction of 1,3-diynes, which can be readily prepared from the coupling reaction of haloalkynes in the presence of CuI. The procedure also can be used for the facile synthesis of 2,5-disubstituted thiophenes.
Sequential synthesis of furans from alkynes: Successive ruthenium(II)- and copper(II)-catalyzed processes
Zhang, Min,Jiang, Huan-Feng,Neumann, Helfried,Beller, Matthias,Dixneuf, Pierre H.
supporting information; experimental part, p. 1681 - 1684 (2009/06/30)
(Chemical Equation Presented) Step in time: 2,5-Disubstituted furans can be prepared from terminal alkynes in one pot using two successive catalytic reactions (see scheme; p-TSA=para-toluene-sulfonic acid). First, a 1,3-dienyl alkyl ether is produced by t
