134029-49-5Relevant articles and documents
An efficient synthesis of resveratrol and a hydroxyl derivative via the Perkin reaction: Cis to trans isomerisation in a demethylation process
Li, Guoxing,Zouand, Yong,Zhang, Xuejing
, p. 657 - 659 (2007)
Two trans polyphenolic stilbenes, Resveratrol and 3,4,4′,5- trans-tetrahydroxystilbene, were prepared in three steps from 4-methoxy phenylacetic acid and methoxylated benzaldehydes via a Perkin reaction. An interesting cis to trans isomerisation occured in the demethylation process in the presence of AII3 and acetonitrile to give resveratrol and 3,4,4′,5-trans-tetrahydroxystilbene with overall yields of 51% and 48% respectively.
Photocatalytic Isomerization of Styrenyl Halides: Stereodivergent Synthesis of Functionalized Alkenes
Zhang, Hao,Xu, Qing,Yu, Lei,Yu, Shouyun
, p. 1472 - 1477 (2019/11/03)
An efficient and general method for the isomerization of styrenyl halides under different photocatalytic conditions (fac-Ir(ppy)3 in methanol for E to Z isomerization and fluorescein in 1,4-dioxane for Z to E isomerization, respectively) is disclosed. A series of stereospecific transformations constitute preliminary validation of this strategy in the synthesis of functionalized alkenes, including two diaryl alkenes, a styrenyl boronic ester and an enyne. The photocatalytic isomerization and subsequent cross coupling reaction can be run in a one-pot manner. The stereodivergent synthesis of all four isomers of a conjugated diene, as well as the antitumor agent DMU-212 and its (Z)-isomer highlights the synthetic applicability of this method.
Water as a Hydrogenating Agent: Stereodivergent Pd-Catalyzed Semihydrogenation of Alkynes
Zhao, Chuan-Qi,Chen, Yue-Gang,Qiu, Hui,Wei, Lei,Fang, Ping,Mei, Tian-Sheng
supporting information, p. 1412 - 1416 (2019/03/07)
Palladium-catalyzed transfer semihydrogenation of alkynes using H2O as the hydrogen source and Mn as the reducing reagent is developed, affording cis- and trans-alkenes selectively under mild conditions. In addition, this method provides an efficient way to access various cis-1,2-dideuterioalkenes and trans-1,2-dideuterioalkenes by using D2O instead of H2O.
Ruthenium-Catalyzed (Z)-Selective Hydroboration of Terminal Alkynes with Naphthalene-1,8-diaminatoborane
Yamamoto, Kensuke,Mohara, Yusei,Mutoh, Yuichiro,Saito, Shinichi
supporting information, p. 17042 - 17047 (2019/10/11)
The metal-catalyzed (Z)-selective hydroboration of terminal alkynes is synthetically challenging due to the usually (E)-selective nature of the hydroboration and the formation of the thermodynamically unstable (Z)-isomer. Herein, we report that N-heterocyclic-carbene-ligated ruthenium complexes catalyze the (Z)-selective hydroboration of terminal alkynes with H-B(dan) (dan = naphthalene-1,8-diaminato), which generates a diverse range of synthetically valuable (Z)-alkenylboranes. Mechanistic studies, particularly the isolation of a catalytically relevant borylruthenium complex, revealed a mechanism that involves the insertion of the alkyne into a Ru-B bond, which provides a catalytic cycle that is distinctly different from that of previously reported (Z)-selective hydroborations. The direct cross-coupling of the obtained (Z)-alkenyl-B(dan) enables the rapid synthesis of biologically active Combretastatin A-4 analogues.
Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes
Armstrong, Megan K.,Goodstein, Madison B.,Lalic, Gojko
supporting information, p. 10233 - 10241 (2018/08/23)
A diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the hydroarylation. Our studies also show that, although the Z- and E-selective hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.
METHODS FOR PHOSPHINE OXIDE REDUCTION IN CATALYTIC WITTIG REACTIONS
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Page/Page column 58; 59; 63, (2014/09/29)
A method for increasing the rate of phosphine oxide reduction, preferably during a Wittig reaction comprising use of an acid additive is provided. A room temperature catalytic Wittig reaction (CWR) the rate of reduction of the phosphine oxide is increased due to the addition of the acid additive is described. Furthermore, the extension of the CWR to semi-stabilized and non-stabilized ylides has been accomplished by utilization of a masked base and/or ylide-tuning.
Synthesis and insect antifeedant activity of stilbene derivatives against Brontispa longissima Larvae
Liu, Ying-Qian,Li, Xiao-Jing,Zhao, Chun-Yan,Lu, Yan,Li, Wen-Qun,Liu, Zhen-Ling,Feng, Gang,Yang, Liu
, p. 2196 - 2206 (2013/07/26)
Continuing our search for natural product-based compounds for the control of B. longissima Larvae, 25 stilbene analogs were synthesized and evaluated for insect antifeedant activity against third-instar larvae of B. longissima for the first time. Among all the tested compounds, especially compounds 3a, 3c, and 6 showed pronounced antifeedant activities with AFC50 values of 0.218, 0.327, and 0.226 mg/mL, respectively. The different antifeedant activity ranges of these compounds indicated that variation of chemical structures in the stilbene skeleton markedly affected the activity profiles of this compound class, and some important SAR information has been revealed from it. In addition, to understand the structural requirements for antifeedant activities of the 25 synthesized stilbene analogs, a comparative molecular field analysis (CoMFA) model, which yielded the leave-one-out (LOO) cross-validated correlation coefficient (q 2) of 0.533 and a non-cross-validated correlation coefficient (r 2) of 0.929, was constructed. Together, these preliminary results may be useful in guiding further modification of stilbenes in the development of potential new antifeedants.
CuI/1,10-phen/PEG promoted decarboxylation of 2,3-diarylacrylic acids: Synthesis of stilbenes under neutral and microwave conditions with an in situ generated recyclable catalyst
Zou, Yong,Huang, Qi,Huang, Tong-Kun,Ni, Qing-Chun,Zhang, En-Sheng,Xu, Tian-Long,Yuan, Mu,Li, Jun
, p. 6967 - 6974 (2013/10/08)
A series of trans- or cis-stilbenes have been synthesized in good to excellent yields via a functional group-dependent decarboxylation process from the corresponding 2,3-diaryl acrylic acids in a neutral CuI/1,10-phen/PEG-400 system under microwave conditions. The in situ generation of the recyclable catalytic complex, the use of environmentally benign solvent PEG-400, the operational simplicity, the short reaction times, as well as the functional group-dependent chemo- and stereo-selectivity have made the decarboxylation process a highly efficient and applicable protocol.
Hydroxyl substitutional effect on selective synthesis of CIS, trans stilbenes and 3-arylcoumarins through perkin condensation
Xiao, Chun-Fen,Zou, Yong,Du, Jian-Li,Sun, Hong-Yi,Liu, Xian-Ke
experimental part, p. 1243 - 1258 (2012/04/04)
The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarins has been described. The regio- and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence or absence of hydroxyl group as well as their positions in the phenyl ring. As a result, practical synthetic strategies were established for preparing various natural stilbenes including combretastatin A-4, pterostilbene, and resveratrol with satisfactory yields (49.2-63.7%). Copyright Taylor & Francis Group, LLC.
Stereodivergent ruthenium-catalyzed transfer semihydrogenation of diaryl alkynes
Li, Jie,Hua, Ruimao
supporting information; experimental part, p. 8462 - 8465 (2011/08/07)
[Ru3(CO)12]-catalyzed transfer semihydrogenation of various functionalized diaryl alkynes with N,N-dimethylformamide (DMF) and water as hydrogen source affords cis- and trans-stilbenes. The stereodivergent approach can be switched by the use of acetic (HOAc) or trifluoroacetic (TFA) acid as additives. The catalytic processes can be applied to the synthesis of analogues of natural products such as cis-combretastatin A-4 and trans-resveratrol. Copyright
