Study of the Wittig reaction of benzyltriphenylphosphonium salt and benzaldehyde via ylide-mediated phase-transfer catalysis

Hwang, Jiann-Jyh; Lin, Ruey-Lih; Shieh, Ruey‐Lone; Jwo, Jing‐Jer

doi:10.1016/s1381-1169(98)00274-x

Cited by 33 publications

(6 citation statements)

References 41 publications

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“…This compound was very unstable, that is why it has been used immediately in the reaction with triphenylfosphine (4.3 g, 15 mmol) in 50 mL of toluene. The reaction mixture was carried on by heating under reflux for 4 h to afford 4-methylthiobenzyl-triphenylphosphonium chloride transfer catalysed Wittig reaction [11,12] (Fig. 3) of phosphonium salt and corresponding commercially available methoxybenzaldehydes (2-methoxybenzaldehyde; 3-methoxybenzaldehyde; anisaldehyde; 2,3-dimethoxybenzaldehyde and 3,5-dimethoxybenzaldehyde).…”

Section: General Considerationmentioning

confidence: 99%

Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities

Mikstacka¹,

Baer‐Dubowska²,

Marcin³

et al. 2008

Mol. Nutr. Food Res.

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Resveratrol (3,5,4'-trihydroxy-trans-stilbene) is a natural stilbene derivative occurring in grapes, peanuts and red wine. Its chemopreventive action has been established in studies on animal models. Recently, numerous classes of compounds with stilbene backbone have been investigated for their biological activity concerning cancer prevention; e. g. resveratrol methyl ethers appeared to be specific and potent inhibitors of cytochromes P450 (CYP) family 1 involved in the activation of procarcinogens. Since the replacement of the 4'-hydroxyl with a thiomethyl group is supposed to reduce toxicity of stilbene derivatives, the purpose of this study was the synthesis and evaluation of a series of 4-thiomethyl-trans-stilbene derivatives differing in a number and position of additional methoxy groups. Their inhibitory potency toward human recombinant CYPs: CYP1A1, CYP1A2 and CYP1B1 have been studied and compared with the effect of resveratrol and its analogues. Among compounds tested, 2-methoxy-4'-thiomethyl-trans-stilbene and 3-methoxy-4'-thiomethyl-trans-stilbene demonstrated the most potent and selective inhibitory effect on CYP1A1 and CYP1B1 activities. The results of our study indicate that modification of stilbene derivatives with thiomethyl group may influence the selectivity and inhibitory potency of these compounds toward P450 isozymes. Thus, it should be considered in developing new chemopreventive agents based on their mechanism of action.

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Section: General Considerationmentioning

confidence: 99%

Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities

Mikstacka¹,

Baer‐Dubowska²,

Marcin³

et al. 2008

Mol. Nutr. Food Res.

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“…2f : ( E )-1-Chloro-3-(3-methylstyryl)benzene, 67 white solid (22.4 mg, 98% yield). 1 H NMR (400 MHz, CDCl 3 ): δ 7.49 (s, 1H), 7.36 (d, J = 8 Hz, 1H), 7.30 (dd, J = 12.0, 8.0 Hz, 3H), 7.25–7.16 (m, 2H), 7.11–7.09 (m, 1H), 7.03 (t, J = 12 Hz, 2H), 2.38 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 139.46, 138.46, 136.87, 134.76, 130.35, 130.00, 129.01, 128.78, 127.51, 127.12, 126.39, 124.84, 123.99, 21.57.…”

Section: Experimental Sectionmentioning

confidence: 99%

H₂O as the Hydrogen Donor: Stereo-Selective Synthesis of E- and Z-Alkenes by Palladium-Catalyzed Semihydrogenation of Alkynes

Shi

Dong

et al. 2023

ACS Omega

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It is very desirable to develop a facile controllable method for selective semihydrogenation of alkynes to alkenes with a cheap and safe hydrogen donor but remains a big challenge. H2O is one of the best choices of the transfer hydrogenation agent of the world, and the development of methods for synthesizing E- and Z-alkenes using H2O as the hydrogen source is worthwhile. In this article, a palladium-catalyzed synthesis of E- and Z-alkenes from alkynes using H2O as the hydrogenation agent was reported. The use of di-tert-butylphosphinous chloride (t-Bu2PCl) and triethanolamine/sodium acetate (TEOA/NaOAc) was essential for the stereo-selective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 48 alkenes, with good yields and high stereoselectivities.

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“…The Wittig reaction has been investigated in aqueous conditions 34,35 . Wittig olefination reactions with stabilized ylides (known as the Wittig-Horner or Horner-Wadsworth-Emmons reaction) are sometimes performed in an organic/aqueous biphasic system 36,37 .…”

Section: Alternative Solvents In Organic Syntheses Watermentioning

confidence: 99%

Green Chemistry in Organic Synthesis

Mishra¹

2022

IJFMR

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The development of the concepts for “Green Chemistry” and the main principles of this field are reviewed. Examples of the application of these principles in different areas of chemistry are included. The frequently used alternative solvents (green solvents – water, PEG, perfluorinated solvents, supercritical liquids) in preparative organic chemistry are described. The present and the future developments of green chemistry in education and organic chemical technology are considered.

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Study of the Wittig reaction of benzyltriphenylphosphonium salt and benzaldehyde via ylide-mediated phase-transfer catalysis

Cited by 33 publications

References 41 publications

Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities

Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities

H₂O as the Hydrogen Donor: Stereo-Selective Synthesis of E- and Z-Alkenes by Palladium-Catalyzed Semihydrogenation of Alkynes

Green Chemistry in Organic Synthesis

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Study of the Wittig reaction of benzyltriphenylphosphonium salt and benzaldehyde via ylide-mediated phase-transfer catalysis

Cited by 33 publications

References 41 publications

Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities

Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities

H2O as the Hydrogen Donor: Stereo-Selective Synthesis of E- and Z-Alkenes by Palladium-Catalyzed Semihydrogenation of Alkynes

Green Chemistry in Organic Synthesis

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Product

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H₂O as the Hydrogen Donor: Stereo-Selective Synthesis of E- and Z-Alkenes by Palladium-Catalyzed Semihydrogenation of Alkynes