102-94-3Relevant articles and documents
Dimethyl sulfoxide mediated elimination reactions in 3-aryl 2,3-dihalopropanoates: Scope and mechanistic insights
Li, Wei,Li, Jianchang,Lin, Melissa,Wacharasindhu, Sumrit,Tabei, Keiko,Mansour, Tarek S.
, p. 6016 - 6021 (2007)
(Chemical Equation Presented) Dimethyl sulfoxide (DMSO) efficiently causes the reductive elimination of 3-aryl 2,3-dibromopropanoates to cinnamates with good yield. With 3-phenyl 2,3-dihalopropanoates, debromination is the major pathway providing 3-phenylacrylate derivatives in high yields, whereas dehydrobromination is a competing pathway with thiophene derivatives. 1H NMR, 81Br NMR, and MS techniques indicated the formation of brominated-DMSO, MeBr, and HBr as byproducts in this transformation with no evidence for the formation of Br2. The dual role of DMSO as a nucleophile and bromine scavenger accounts for the products formed in this reaction.
Excited-state Reactions of Triphenylphyrylium Ion with Cinnamate Derivatives: Triplet-mediated Isomerization and Singlet-mediated Dimerization
Ramamurthy, P.,Morlet-Savary, F.,Fouassier, J. P.
, p. 465 - 470 (1993)
Excited-state reactivity of 2,4,6-triphenylpyrylium ion (TPP+) with cinnamates has been studied by fluorescence quenching and laser flash photolysis experiments.Electron-transfer reactions between cinnamates and excited states of TPP+ are reported.The pyryl radical (TPP*) has been observed as an intermediate.In the singlet manifold, dimerization product(s) are reported and in the triplet manifold the trans-cis isomerization product is reported.Selectivity of oxygen in the product formation is observed.This is one of the few systems in which both isomerization and dimerization mechanisms are operating together through a radical cation intermediate.For the first time the dimerization of cinnamate derivatives via a radical cation is reported.
Organoaluminum-promoted cycloaddition of trialkylsilylketene with aldehydes: A new, stereoselectie approach to cis-2-oxetanones and 2(Z)-alkenoic acids
Concepcion,Maruoka,Yamamoto
, p. 4011 - 4020 (1995)
The exceptionally bulky methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR) can be successfully utilized as a highly efficient Lewis acid for achieving high stereoselectivity in the cycloaddition of trialkylsilylketene with aldehydes. This method serves as a highly effective route to the synthesis of cis-2-oxetanones from saturated aldehydes, and the synthesis of 2(Z)-alkenoic acids from aromatic and α,β-unsaturated aldehydes.
Highly Efficient Pd-Catalyzed Coupling of Arenes with Olefins in the Presence of tert-Butyl Hydroperoxide as Oxidant
Jia, Chengguo,Lu, Wenjun,Kitamura, Tsugio,Fujiwara, Yuzo
, p. 2097 - 2100 (1999)
(matrix presented) ArH : benznoid and non-benzenoid. R = H, CH3, Ph. R1 = Ph, CO2Et, COMe, CHO, CO2H, CN. The oxidative coupling of arenes with olefins has been performed efficiently in the presence of catalytic amounts of palladium acetate and benzoquinone (BQ) with tert-butyl hydroperoxide as the oxidant in up to 280 turnover numbers (TON). The catalytic system is especially active for the coupling of heterocycles such as furans and indole with activated olefins. The reaction is highly regio-and stereoselective, giving trans-olefins predominantly.
K2PtCl4/AgOTf as a highly active catalyst for hydroarylation of propiolic acids with arenes
Oyamada, Juzo,Kitamura, Tsugio
, p. 1430 - 1431 (2005)
A new and efficient K2PtCl4/AgOTf catalyst for the hydroarylation of propiolic acid was found. The hydroarylation of propiolic acids gave predominantly (Z)-cinnamic acid derivatives in high yields. The K2PtCl4/AgOTf catalyst showed a high activity to less reactive benzene. Copyright
Hypervalent iodine reagents enable chemoselective deboronative/decarboxylative alkenylation by photoredox catalysis
Huang, Hanchu,Jia, Kunfang,Chen, Yiyun
, p. 1881 - 1884 (2015)
Chemoselective C(sp3)-C(sp2) coupling reactions under mild reaction conditions are useful for synthesizing alkyl-substituted alkenes having sensitive functional groups. Reported here is a visible-light-induced chemoselective alkenylation through a deboronation/decarboxylation sequence under neutral aqueous reaction conditions at room temperature. This reaction represents the first hypervalent-iodineenabled radical decarboxylative alkenylation reaction, and a novel benziodoxole-vinyl carboxylic acid reaction intermediate was isolated. This C(sp3/sup>)-C(sp2) coupling reaction leads to aryl-and acyl-substituted alkenes containing various sensitive functional groups. The excellent chemoselectivity, stable reactants, and neutral aqueous reaction conditions of the reaction suggest future biomolecule applications.
Photodimerization of trans-Cinnamic Acid in a Bilayer of Dimethyldioctadecylammonium Bromide
Nakamura, Tomotaka,Takagi, Katsuhiko,Sawaki, Yasuhiko
, p. 909 - 914 (1998)
The photochemistry of trans-cinnamic acid (trans-1) was studied in a cast film of dimethyldioctadecylammonium bromide (2), deposited from aqueous dispersions as a crystalline solid by the spontaneous vaporization of water. UV irradiation of the cast film resulted in a highly selective formation of the syn-Head-to-Head dimer, suggesting a parallel orientation of trans-1 within a bilayer film. Analyses with X-ray diffraction, differential scanning calorimetry, and IR spectra revealed the formation of a bilayer structure of 2 in which the molecules of trans-1 are dissolved to interact with 2 of the polar head groups. The photoreactivity of trans-1 in the cast film was found to be dramatically suppressed by heating at 40-60 °C, which is attributed to an improvement in the crystallinity of the bilayer.
Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids
Lu, Xiao-Yu,Li, Jin-Song,Wang, Shi-Qun,Zhu, Yu-Jing,Li, Yue-Ming,Yan, Lu-Yu,Li, Jia-Mei,Wang, Jin-Yu,Zhou, Hai-Pin,Ge, Xiu-Tao
, p. 11123 - 11126 (2019)
A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as a mixture of diastereomers favoring the anti diastereomer of the cyclic epoxides. This work provides a method for the modification of complex organic molecules containing α,β-unsaturated carboxylic acids.
Highly selective semihydrogenation of phenylalkynes to (Z)-styrenes using hantzsch ester 1,4-dihydropyridine catalyzed by Pd/C
Zhao, Yankai,Liu, Qiang,Li, Jing,Liu, Zhongquan,Zhou, Bo
, p. 1870 - 1872 (2010)
Various alkynes have been selectively reduced to the corresponding Z-alkenes catalyzed by Pd/C using Hantzsch ester 1,4-dihydropyridine as the hydrogen source. Georg Thieme Verlag Stuttgart.
Stereospecific electrochemical carboxylation of β-bromostyrene by use of nickel(II) catalyst
Kuang, Chunxiang,Yang, Qing,Senboku, Hisanori,Tokuda, Masao
, p. 528 - 529 (2005)
Electrochemical carboxylation of (E)- and (Z)-β-bromostyrenes (1) under an atmospheric pressure of carbon dioxide with a platinum cathode and a magnesium anode in the presence of 20 mol % of NiBr2·bpy proceeded with retention of stereochemistry to give the corresponding (E)- or (Z)-cinnamic acids (2). The stereochemical outcome of nickel(II)-catalyzed electrochemical carboxylations was discussed by comparison with predominant formation of a (Z)-isomer from either (E)- or (Z)-β-bromostyrenes. Copyright
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Wright
, (1937)
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Selective homogeneous palladium(0)-catalyzed hydrogenation of alkynes to (Z)-alkenes
Van Laren, Martijn W.,Elsevier, Cornelis J.
, p. 3715 - 3717 (1999)
Zero-valent palladium precatalysts containing rigid bidentate bis(arylimino)acenaphthene ligands (shown schematically) facilitate the highly stereoselective homogeneous catalytic hydrogenation of alkynes to (Z)- alkenes. Internal, terminal, aryl-substituted, and cyclic alkynes are suitable substrates, as are some enynes, which are chemoselectively hydrogenated to dienes. E=CO2Me; R1, R2 = 4-OCH3, 4-CH3, 2,6-(CH3)2.
Rao,Filler
, p. 471 (1976)
Templating photodimerization of trans-cinnamic acids with cucurbit[8]uril and γ-cyclodextrin
Pattabiraman, Mahesh,Natarajan, Arunkumar,Kaanumalle, Lakshmi S.,Ramamurthy
, p. 529 - 532 (2005)
(Chemical Equation Presented) Cucurbit[8]uril and γ-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with trans-cinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.
Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie
supporting information, p. 8829 - 8842 (2021/06/30)
Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.
Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters
Kim, Byungjun,Lee, Sarah Yunmi,Song, Yuna
supporting information, p. 11052 - 11055 (2021/10/30)
We report here a silver-catalyzed method for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. This process proceeds through asymmetric conjugate addition of glycine imine esters to a broad range of β-substituted α,β-unsaturated perfluorophenyl esters followed by lactamization. By leveraging catalyst control and stereospecificity of the 1,4-addition process, all four product stereoisomers containing two adjacent stereocenters are accessible with high stereoselectivity.
Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of: Z-cinnamic acid derivatives
Rodríguez, Roció B.,Rodríguez, Roció B.,Zapata, Ramiro L.,Salum, Mariá L.,Salum, Mariá L.,Erra-Balsells, Rosa,Erra-Balsells, Rosa
, p. 819 - 830 (2020/07/03)
Photoisomerization of a series of substituted E-cinnamic acids in MeCN in their acid forms and as their corresponding protic ionic liquids (PILs) with light of 300 nm is studied. The nature, strength, number, and position effects of substituents on the photochemical behavior of E-cinnamic derivatives are investigated. The photosensitization of the reaction in the presence of Michler's ketone is also studied at 366 nm and it demonstrates that the triplet-excited state is involved in the reaction. As the presence of n-butylamine needed to form the PILs significantly increases the photoproduct yields in all cases, the role of the PILs is also discussed. Thus, understanding of these fundamental aspects has allowed us to establish an excellent and practical synthetic protocol for successfully synthesizing Z-cinnamic acids. This journal is