69916-34-3Relevant academic research and scientific papers
Synthesis of 3-Carbonyl Trisubstituted Furans via Pd-Catalyzed Aerobic Cycloisomerization Reaction: Development and Mechanistic Studies
Barboza, Amanda A.,Neto, Attilio Chiavegatti,Rosset, Isac G.,Jardim, Guilherme A. M.,Ferreira, Marco A. B.
, p. 3923 - 3942 (2021/04/02)
Herein, we report the synthesis of 3-carbonyl-trisubstituted furans via Pd-catalyzed oxidative cycloisomerization reactions of 2-alkenyl-1,3-dicarbonyl scaffolds, using molecular oxygen as the sole oxidant to regenerate active palladium catalytic species, featuring good functional tolerance and mild reaction conditions. Deep investigation of intermediates and transition states of the reaction mechanism were conducted via experimental and DFT studies, providing a detailed mechanistical profile. The new developed methodology presents a greener alternative to Wacker-type cycloisomerizations and avoids the use of stoichiometric amounts of oxidants and strong acid additives.
Acid-Promoted One-Pot Synthesis of Substituted Furan and 6-Methylpyrazin-2(1 H)-one Derivatives via Allene Intermediate Formed in Situ
Lei, Jie,Xu, Zhi-Gang,Tang, Dian-Yong,Li, Yong,Xu, Jia,Li, Hong-Yu,Zhu, Jin,Chen, Zhong-Zhu
, p. 292 - 297 (2018/05/24)
Under the acidic conditions, substituted furans were constructed from γ-alkynyl ketones through corresponding allene intermediates in one-pot. The methodology was also tailored to a series of the Ugi reaction products for the synthesis of 6-methylpyrazin-2(1H)-one derivatives. The current method offered significant advantages for the combinatorial applications of these chemical scaffolds.
nBu4NI-catalyzed C–C bond formation to construct 2-carbonyl-1,4-diketones under mild conditions
Lv, Yunhe,Pu, Weiya,Niu, Jiejie,Wang, Qingqing,Chen, Qian
, p. 1497 - 1500 (2018/03/13)
An nBu4NI-catalyzed oxidative cross-dehydrogenative-coupling of β-dicarbonyl compounds with acetone under mild reaction conditions is described. This methodology provides a straightforward pathway to synthesize 2-carbonyl-1,4-diketones and feat
Preparation of polysubstituted dihydrofurans through a PhI(OAc)2-promoted haloenolcyclization of olefinic dicarbonyl compounds
Liu, Ji,Liu, Qing-Yun,Fang, Xing-Xiao,Liu, Gong-Qing,Ling, Yong
, p. 7454 - 7460 (2018/10/24)
A metal-free cyclization of olefinic dicarbonyl compounds for the synthesis of various 5-halomethyl-4,5-dihydrofurans is presented. Using (diacetoxyiodo)benzene as the reaction promoter and halotrimethylsilane as the halogen source, the intramolecular hal
Thulium Triflate Catalyzed Hydration of 2-Substituted 4-Alkynones
Chang,Cheng
supporting information, p. 1931 - 1935 (2016/08/09)
We report on a facile synthetic route for the preparation of substituted 1,4-diketones by thulium triflate mediated hydration of substituted 4-alkynones in MeNO2 at 25 °C for five hours. The products were obtained in moderate to high yields.
Bi(OTf)3-mediated cycloisomerization of γ-alkynyl arylketones: Application to the synthesis of substituted furans
Chang, Meng-Yang,Cheng, Yu-Chieh,Lu, Yi-Ju
supporting information, p. 1264 - 1267 (2015/03/14)
A novel Bi(OTf)3-mediated cycloisomerization of γ-alkynyl arylketones 4, 7, or 10 with molecular sieve (MS) in MeNO2 affords 3-substituted furans 3, 8, or 11 at rt for 3 h in moderate to good yields. The method provides mild, less-to
The rearrangement of tert -butylperoxides for the construction of polysubstituted furans
Zheng, Xiaojian,Lu, Shenglin,Li, Zhiping
supporting information, p. 5432 - 5435 (2013/11/19)
The Bronsted acid catalyzed rearrangement of tert-butyl peroxides provides a new strategy to construct 2,3-disubstituted furans via 1,2-aryl migration. In addition, tert-butyl peroxides could also be transformed into 2,3,5-trisubstituted or 2,5-disubstituted furans through a sequence of base-catalyzed Kornblum-DelaMare rearrangements and acid-promoted Paal-Knorr reactions.
Transition-metal-catalyzed domino reactions: Efficient one-pot regiospecific synthesis of highly functionalized polysubstituted furans from electron-deficient alkynes and 2-Yn-1-ols
Cao, Hua,Jiang, Huanfeng,Huang, Huawen
experimental part, p. 1019 - 1036 (2011/05/14)
Based on the reactive behavior of different transition-metal catalysts, three methods for the synthesis of highly functionalized polysubstituted furan derivatives are presented: (i) copper(I) iodide catalyzed regiospecific synthesis of furan aldehydes/ketones from alkynols and diethyl but-2-ynedioate under atmospheric pressure; (ii) nano-Cu-catalyzed domino process for the regioselective synthesis of -carbonylfurans from readily accessible starting materials; (iii) silver-catalyzed one-pot cyclization in toluene at 50 C for the synthesis of furan derivatives. It was notably that all the domino reactions were smooth under mild conditions with commercially available catalysts, and afforded highly functionalized furans in moderate to good yields. As we know, furans derivatives are extremely useful organic molecules used as synthetic building blocks for the synthesis of more elaborate heterocyclic compounds. Georg Thieme Verlag Stuttgart.
Pd-catalyzed cycloisomerization-allylation of 4-alkynones: Synthesis of 5-homoallylfuran derivatives
Saito, Akio,Enomoto, Yohei,Hanzawa, Yuji
scheme or table, p. 4299 - 4302 (2011/08/22)
In the presence of Pd2(dba)3-tBu3P catalyst and Cs2CO3, cycloisomerization-allylation reactions of 4-alkynone derivatives with allyl carbonates in MeCN proceed in 5-exo mode to give highly-substituted furans having homoallyl groups at 5-position.
Silver-catalyzed one-pot cyclization reaction of electron-DEficient alkynes and 2-Yn-1-ols: An efficient domino process to polysubstituted furans
Cao, Hua,Jiang, Huanfeng,Mai, Ronghuan,Zhu, Shifa,Qi, Chaorong
supporting information; experimental part, p. 143 - 152 (2010/06/17)
Transition metal-catalyzed domino reactions have been used as powerful tools for the preparation of polysubstituted furans in a one-pot manner. In this paper, an efficient synthetic method was developed for the construction of tri- or tetrasubstituted furans from electron-deficient alkynes and 2-yn-1-ols by a silver-catalyzed domino reaction. It is especially noteworthy that a 2,3,5-trisubstituted 4-ynylfuran was formally obtained in an extremely direct manner without tedious stepwise synthesis. In addition, regio-isomeric furans were observed when substituted aryl alkynyl ketones were employed. This methodology represents a highly efficient synthetic route to electron-deficient furans for which catalytic approaches are scarce. The reaction proceeds efficiently under mild conditions with commercially available catalysts and materials.
