7560-69-2Relevant academic research and scientific papers
Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones
He, Chun-Ting,Han, Xiao-Li,Zhang, Yan-Xue,Du, Zhen-Ting,Si, Chang-Mei,Wei, Bang-Guo
supporting information, p. 457 - 466 (2021/01/29)
An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is
Gem-Digold Acetylide Complexes for Catalytic Intermolecular [4 + 2] Cycloaddition: Having Two Gold Centers Is Better for Asymmetric Catalysis
Nanko, Masaki,Shibuya, Satoru,Inaba, Yuya,Ono, Soichiro,Ito, Shigekazu,Mikami, Koichi
supporting information, p. 7353 - 7357 (2018/10/15)
Gold(I)-catalyzed highly enantioselective intermolecular [4 + 2] cycloaddition is shown with ynones and cyclohexadiene. Various bicyclo[2.2.2]octadiene derivatives are produced in high yields (up to 99%) with good enantioselectivity (up to 96% ee). Key to the success is generation of the gem-digold terminal alkyne as a catalytic on-cycle species. As proof of the gem-digold catalysis, a positive nonlinear effect is clarified between the ee's of the ligand and the cycloadduct.
Propargylic C[sbnd]H activation using a Cu(II) 2-quinoxalinol salen catalyst and tert-butyl hydroperoxide
Black, Clayton C.,Gorden, Anne E.V.
supporting information, p. 803 - 806 (2018/02/06)
The oxidation of alkynes to α,β-acetylenic carbonyls was achieved using only 1 mol% of a Cu(II) 2-quinoxalinol salen catalyst with tert-butyl hydroperoxide. These reactions proceed under mild conditions (70 °C) with excellent selectivity, producing yields up to 78%, and were used on a variety of alkyne substrates to produce the desired corresponding α,β-acetylenic ketones. In addition, these reactions can be run under aqueous conditions using a sulfonated version of the 2-quinoxalinol salen with good yields, reducing the need for volatile organic solvents.
A propargyl alcohol oxidation system acetylenic ketone method
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Paragraph 0045; 0046; 0047, (2016/10/10)
The invention provides a method for preparing acetylenic ketone through oxidizing propargyl alcohol. The method comprises the following steps: in a liquid phase, taking 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as the catalyst, nitric acid as the co-catalyst, and oxygen gas as the oxidant, and oxidizing propargyl alcohol in an organic solvent so as to produce acetylenic ketone. The method has the advantages of mild conditions, convenient operation, no metal, and little pollution, and is a green and environment-friendly novel method for preparing ketone through oxidizing alcohol with a non-metal catalyst.
Mild propargylic oxidation using a diacetoxyiodobenzene/tert-butyl hydroperoxide protocol
Zhao, Yi,Ng, Angela Wan Ting,Yeung, Ying-Yeung
, p. 4370 - 4372 (2014/07/22)
A mild propargylic oxidation of alkynes is reported using a diacetoxyiodobenzene/tert-butyl hydroperoxide (DIB/TBHP) protocol. The reactions proceed smoothly at 0 °C and a number of α,β-unsaturated alkynoic ketones are obtained.
Palladacycle-catalyzed reaction of bicyclic alkenes with terminal ynones: Regiospecific synthesis of polysubstituted furans
Ge, Guang-Cun,Mo, Dong-Liang,Ding, Chang-Hua,Dai, Li-Xin,Hou, Xue-Long
supporting information, p. 5756 - 5759 (2013/01/15)
A new synthetic strategy to access polysubstituted furans regiospecifically has been developed using simple bicyclic alkenes and terminal ynones as starting materials with palladacycles as unique active catalysts. A rational mechanism has also been proposed. This reaction features mild reaction conditions, easily available starting materials and palladacycle catalysts, a wide substrate scope, and high regiospecificity.
Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings
Ardolino, Michael J.,Morken, James P.
supporting information; scheme or table, p. 8770 - 8773 (2012/07/02)
The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.
N-Vinylpyridinium tetrafluoroborate salts as reagents for the stereoselective and regioselective synthesis of symmetrical (2E,4E)-1,6-dioxo-2,4-dienes
Gao, Ge,Brown, Neil,Minatoya, Machiko,Buszek, Keith R.
scheme or table, p. 6491 - 6494 (2009/04/06)
We had previously demonstrated the utility of N-vinylpyridinium tetrafluoroborate salts as novel electrophilic coupling partners in Pd(0)-catalyzed Suzuki cross-coupling reactions with aryl and vinyl boronic acids. We now report that these crystalline, air-stable, and non-hygroscopic salts are also useful reagents for the synthesis of symmetrical (2E,4E)-1,6-dioxo-2,4-dienes (diene diones), which in turn are valuable starting materials for the synthesis of various five-membered heterocycles. The optimization of reaction conditions and the scope and limitations of the reductive dimerization are discussed.
Calcium phosphate-vanadate apatite (CPVAP)-catalyzed aerobic oxidation of propargylic alcohols with molecular oxygen
Maeda, Yasunari,Washitake, Yosuke,Nishimura, Takahiro,Iwai, Keisuke,Yamauchi, Takayoshi,Uemura, Sakae
, p. 9031 - 9036 (2007/10/03)
Calcium phosphate-vanadate apatite (CPVAP) works effectively as a catalyst for the aerobic oxidation of propargylic alcohols to the corresponding carbonyl compounds under an atmospheric pressure of molecular oxygen. Moreover, CPVAP can be readily separated by filtration and reused at least 10 times without appreciable loss of the catalytic activity.
Oxovanadium complex-catalyzed aerobic oxidation of propargylic alcohols
Maeda, Yasunari,Kakiuchi, Nobuyuki,Matsumura, Satoshi,Nishimura, Takahiro,Kawamura, Takashi,Uemura, Sakae
, p. 6718 - 6724 (2007/10/03)
A catalytic system consisting of vanadium oxyacetylacetonate [VO(acac)2] and 3 A molecular sieves (MS3A) in acetonitrile works effectively for the aerobic oxidation of propargylic alcohols [R1CH-(OH)C≡CR2] to the corresponding carbonyl compounds under an atmospheric pressure of molecular oxygen. Although the reactivity of α-acetylenic alkanols (R1 = alkyl) is lower compared to that of the alcohols of R1 = aryl, alkenyl, and alkynyl, the use of VO(hfac)2 as a catalyst and the addition of hexafluoroacetylacetone improve the product yield in these cases. A catalytic cycle involving a vanadium(V) alcoholate species and β-hydrogen elimination from it has been proposed for this oxidation.
