- Transition-metal-catalyzed domino reactions: Efficient one-pot regiospecific synthesis of highly functionalized polysubstituted furans from electron-deficient alkynes and 2-Yn-1-ols
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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.
- Cao, Hua,Jiang, Huanfeng,Huang, Huawen
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- Iron-catalyzed domino process for the synthesis of α-carbonyl furan derivatives via one-pot cyclization reaction
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(Figure presented) The Fe(ClO4)3-catalyzed intramolecular rearrangement/cyclization/oxidation reaction sequence for the synthesis of α-carbonyl furan derivatives from electron-deficient alkynes and 2-yn-1-ols is reported.
- Jiang, Huanfeng,Yao, Wenjuan,Cao, Hua,Huang, Huawen,Cao, Derong
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experimental part
p. 5347 - 5350
(2010/10/20)
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- Silver-catalyzed one-pot cyclization reaction of electron-DEficient alkynes and 2-Yn-1-ols: An efficient domino process to polysubstituted furans
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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.
- Cao, Hua,Jiang, Huanfeng,Mai, Ronghuan,Zhu, Shifa,Qi, Chaorong
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supporting information; experimental part
p. 143 - 152
(2010/06/17)
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- Nano-Cu2O-catalyzed formation of C-C and C-O bonds: One-pot domino process for regioselective synthesis of α-carbonyl furans from electron-deficient alkynes and 2-Yn-1-ols
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The formation of carboncarbon and carbon-oxygen bonds continues to be an active and challenging field of chemical research. Nanoparticle catalysis has attracted considerable attention owing to its environmentally benign and high activity toward the reactions. Herein, we described a novel and effective nano-Cu2O-catalyzed one-pot domino process for the regioselective synthesis of α-carbonyl furans. Various electron-deficient alkynes with 2-yn-1-ols underwent this process smoothly in moderate to good yields in the presence of air at atmospheric pressure. It is especially noteworthy that a novel 2,4,5-trisubstituted 3-ynylfuran was formed in an extremely direct manner without tedious stepwise synthesis. Additionally, as all of the starting materials are readily available, this method may allow the synthesis of more complex α-carbonyl furans. An experiment to elucidate the mechanism suggested that the process involved a carbene intermediate.
- Cao, Hua,Jiang, Huanfeng,Yuan, Gaoqing,Chen, Zhengwang,Qi, Chaorong,Huang, Huawen
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supporting information; experimental part
p. 10553 - 10559
(2010/10/21)
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