- Ruthenium-catalysed oxidative coupling of vinyl derivatives and application in tandem hydrogenation
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The first ruthenium-catalyzed oxidative homo- and cross-coupling of exclusive vinyl derivatives giving highly valued 1,3-diene building blocks is reported. The catalytic system is based on readily available reagents and it mainly delivers the E,E isomer. This methodology also enables the synthesis of adipic acid ester derivatives in a one-pot fashion after in situ ruthenium-catalyzed hydrogenation.
- Abuhafez, Naba,Bruneau, Christian,Gramage-Doria, Rafael,Kamaraj, Raghu,Ruffin, Hervé
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p. 5772 - 5776
(2021/09/10)
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- Synthesis method of (E, E) -1 and 3 - conjugated dienes
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The invention discloses a synthesis method of (Z,Z)-1,3-conjugated diene. The synthesis method comprises the following steps of, in a dioxane/water solvent system, heating a propiolate derivative andtriethylene diamine in the presence of an inert gas, and reacting to generate the (Z,Z)-1,3-conjugated diene. The method is simple, no noble metal is used as a catalyst; the cost is low, and further,an environment cannot be polluted.
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Paragraph 0026-0027
(2021/07/17)
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- Pd-catalyzed oxidative homo-coupling of acrylates and aromatic alkenes for the conjugated diene synthesis
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We developed a bidentate monoanionic nitrogen ligand that was effective in the Pd-catalyzed oxidative homo-coupling reaction of acrylates and aromatic alkenes. In the presence of Pd(OAc)2/ligand several conjugated dienes were obtained in good yields with high stereoselectivities.
- Zhu, Ting,Li, Zhen,Xiao, Fanhua,Duan, Wei-Liang
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supporting information
p. 3238 - 3241
(2018/07/21)
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- A cyclohexene - 1, 4 - dicarboxylic acid diester preparation method (by machine translation)
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The invention discloses a cyclohexene - 1, 4 - dicarboxylic acid diester preparation method. The preparation method uses anti-, anti-- hexadiene diallyl two acid as raw material, access to a certain pressure of ethylene gas, keep a certain reaction temperature, under the action of the acidic catalyst, with the low-carbon aliphatic alcohol reaction, through esterification with the Diels - Alder cycloaddition reaction, high selectivity to make the cyclohexene - 1, 4 - dicarboxylic acid diester; the acid catalyst is a proton acid and/or a solid acid catalyst; the low carbon fatty alcohol is C1 - C4 A polyol or diol in the one or more than two. Ethylene pressure is 0.1 - 10 mpa; the reaction temperature is 100 - 300 °C; the reaction time is 0.1 - 10 hours. In the anti-, anti-- hexadiene diallyl two acid conversion is 99% when, cyclohexene - 1, 4 - dicarboxylic acid diester total selectivity can be up to 99% or more. (by machine translation)
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Paragraph 0037; 0038-0079; 0080; 0081; 0082; 0083; 0084
(2017/06/21)
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- Production of Diethyl Terephthalate from Biomass-Derived Muconic Acid
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We report a cascade synthetic route to directly obtain diethyl terephthalate, a replacement for terephthalic acid, from biomass-derived muconic acid, ethanol, and ethylene. The process involves two steps: First, a substituted cyclohexene system is built through esterification and Diels-Alder reaction; then, a dehydrogenation reaction provides diethyl terephthalate. The key esterification reaction leads to improved solubility and modulates the electronic properties of muconic acid, thus promoting the Diels-Alder reaction with ethylene. With silicotungstic acid as the catalyst, nearly 100 % conversion of muconic acid was achieved, and the cycloadducts were formed with more than 99.0 % selectivity. The palladium-catalyzed dehydrogenation reaction preferentially occurs under neutral or mildly basic conditions. The total yield of diethyl terephthalate reached 80.6 % based on the amount of muconic acid used in the two-step synthetic process.
- Lu, Rui,Lu, Fang,Chen, Jiazhi,Yu, Weiqiang,Huang, Qianqian,Zhang, Junjie,Xu, Jie
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supporting information
p. 249 - 253
(2016/01/25)
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- METHOD FOR PRODUCING MUCONIC ACIDS AND FURANS FROM ALDARIC ACIDS
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The present invention relates to selective catalytic dehydroxylation method of aldaric acids for producing muconic acid and furan chemicals, which can be used directly in fine chemical and polymer applications (FCA/FDCA) and as intermediates in the preparation of industrially significant chemicals, such as terephthalic acid, adipic acid, caprolactone, caprolactam, nylon 6.6, 1,6-hexanediol and multiple pharmaceutical building blocks (MA/MAME).
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Page/Page column 8; 9
(2016/01/01)
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- PDC-mediated tandem oxidative-wittig olefination
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A convenient tandem oxidative-Wittig olefination of a primary alcohols to α,β-unsaturated compounds using pyridinium dichromate (PDC) is described.
- Dhumaskar, Kashinath L.,Bhat, Chinmay,Tilve, Santosh G.
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supporting information
p. 1501 - 1506
(2014/05/20)
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- Rhodium-catalyzed decarboxylative and dehydrogenative coupling of maleic acids with alkynes and alkenes
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The dehydrogenative coupling of maleic acids with alkynes proceeds smoothly accompanied by decarboxylation under rhodium catalysis to produce variously substituted α-pyrone derivatives. The catalyst system is also applicable to the coupling with 1,3-diyne
- Itoh, Masaki,Shimizu, Masaki,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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p. 11427 - 11432
(2013/12/04)
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- DMP-mediated one-pot oxidative olefination of silyl ethers
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Silyl ethers of arylic, allylic, propargylic and unactivated alcohols could be deprotected and oxidized with Dess-Martin periodinane, and the resulting aldehydes could be directly converted to the corresponding α,β- unsaturated esters in one pot with stabilized phosphoranes. Good selectivities were achieved upon a variety of protecting groups of alcohol by using this method. Other advantages of the protocol included simplicity of operations and high efficiency, as well as good to excellent yields.
- Deng, Guisheng,Xu, Baihua,Liu, Chunyu
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p. 5818 - 5821
(2007/10/03)
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- Domino primary alcohol oxidation-wittig reaction: Total synthesis of ABT-418 and (E)-4-oxonon-2-enoic acid
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Domino oxidation of primary alcohols to α,β-unsaturated compounds using the combination of PCC-NaOAc and stabilized Wittig reagent and its application towards total synthesis of ABT-418 and 4-oxonon-2-enoic acid is described.
- Shet, Jyoti,Desai, Vidya,Tilve, Santosh
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p. 1859 - 1863
(2007/10/03)
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- Palladacyclopentadiene complexes with mono- and didentate imidato ligands: Synthesis, hemilabile behaviour and catalytic application in the stille reaction
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The binuclear hydroxo complex [NBu4]2[Pd 2(C4(COOMe)4)2-(μ-OH) 2] (1) has been prepared by addition of two equivalents of NBu 4OH to polymeric [Pd{C4(COOMe)4}]n. Complex 1 has been successfully employed as a precursor to three novel binuclear imidate-bridged complexes [NBu4]2[Pd2-(C 4(COOMe)4)2(μ-imidate)2] [imidate = succinimidate (sue) 2, phthalimidate (pht) 3 or maleimidate (mal) 4] in which the imidate group displays a bidentate N,O-coordination mode. The hemilabile behaviour of the imidate ligands has been investigated by reaction with a variety of P, N and S ligands, affording the corresponding mononuclear derivatives [NBu4][Pd{C4(COOMe)4}(imidate)L] [L = PPh3 (2a, 3a or 4a), P(p-C6H4F)3 (2b, 3b or 4b), PBu3 (2c, 3c or 4c), py (2d, 3d or 4d), p-MeC 6H4NH2 (2e, 3e or 4e), tetrahydrothiophene (2f, 3f or 4f)] with terminal N-bonded imidate ligands. The characterization of the new complexes involved spectroscopic methods (IR, FAB, 1H, 13C, 19F and 31P NMR) and X-ray crystallographic analysis for 1, 4b and 4e. The mononuclear derivatives are shown to catalyse the Stille cross-coupling of benzyl bromide 7 with ethyl Z-vinylstannyl carboxylate (8) in high yields. Yields and reaction times are dependent on the presence and type of imidate ligand, which suggests an important role for it in the catalytic cycle. Wiley-VCH Verlag GmbH and Co. KGaA, 69451 Weinheim, Germany, 2004.
- Serrano, Jose Luis,Fairlamb, Ian J. S.,Sanhez, Gregorio,Garcia, Luis,Perez, Jose,Vives, Jorge,Lopez, Gregorio,Crawforth, Catherine M.,Taylor, Richard J. K.
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p. 2706 - 2715
(2007/10/03)
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- The in situ oxidation-Wittig reaction of α-hydroxyketones
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In situ oxidation-Wittig methodology has been applied to α-hydroxyketones avoiding the problems normally associated with α-ketoaldehydes; the procedure is practically simple, and in many cases gives high yields of the product γ-ketocrotonates; the procedu
- Runcie, Karen A.,Taylor, Richard J. K.
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p. 974 - 975
(2007/10/03)
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- One-pot oxidation and Wittig olefination of alcohols using o-iodoxybenzoic acid and stable Wittig ylide
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Benylic, allylic, and propargylic alcohols, as well as diols, can be oxidized with o-iodoxybenzoic acid (IBX) in the presence of stabilized Wittig ylide to generate α,β-unsaturated ester in one pot. This is useful when the intermediate aldehydes are unsta
- Maiti,Yadav
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p. 1499 - 1506
(2007/10/03)
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- A comparison of Wittig and Wittig Horner (wadsworth emmons) reagents in reactions with some α-dicarbonyl compounds
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For the α-dicarbonyl compounds RCOCHO studied where R=H, Me or Ph it was found that the use of Wittig reagents resulted in higher overall yields of the expected products and that with neither type of reagent could the product OCHCH=CHCO2Et from glyoxal be isolated.
- Mawaziny, Sheila,Makky, Sadiah
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- Ni-catalyzed homocoupling of 3-halopropenoates in the presence of water: Formation of hexenedioates
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Homocoupling of (Z)-3-halopropenoates using a catalytic amount of NiCl2 and Zn in the presence of water in pyridine afforded a mixture of (Z)- and (E)-3-hexenedioates.
- Kotora, Martin,Matsumura, Hiroshi,Takahashi, Tamotsu
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p. 236 - 237
(2007/10/03)
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- Asymmetric synthesis of bicyclopropane derivatives
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Both syn- and anti-bicyclopropane derivatives have been efficiently prepared with good relative and absolute stereocontrol using reagent controlled asymmetric cyclopropanation reactions. Double Simmons-Smith cyclopropanation of 2,4-dien-1-ols stereoselectively gave the corresponding anti-bicyclopropane derivatives.
- Barrett, Anthony G. M.,Doubleday, Wendel W.,Tustin, Gary J.
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p. 15325 - 15338
(2007/10/03)
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- ALKYLATIVE ELIMINATIONS. CONJUGATED DIENECARBOXYLATES FROM (ETHOXYCARBONYLCYCLOPROPYL)CARBINYL ANIONS STABILIZED BY SULFUR GROUPS
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(Ethoxycarbonylcyclopropyl)carbinyl anions stabilized by phenylsulfonyl or phenylthio groups undergo one-pot nucleophilic ring fission, alkylation and elimination of the sulfur function to give substituted dienoates or dienedioates.
- Tomazic, A.,Ghera, E.
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p. 4349 - 4352
(2007/10/02)
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