- Synthesis of 1,2-diarylethylenes by Pd-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes
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Background: Substituted olefins are versatile functional groups and intermediates in chemistry, medicine, electronics, and optics and materials science fields because of their unique properties. One important class of substituted olefins 1,2-diarylethylenes have attracted considerable attention due to their presence in both natural products and pharmacologically active substances. Methods: In this paper, we developed a one-pot two-step coupling reaction of aryl aldehydes, tosylhydrazide with benzyl halides by using inexpensive Pd(PPh3)4 as catalyst, leading to a variety of 1,2- diphenylethenes derivatives with moderate to good yields. Results: The desired 1,2-diarylethylenes were obtained in 46-96% yields via Pd(0)-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes. Conclusion: The catalytic system presented here enables the use of easily accessible starting materials and good functional group tolerance.
- Shen, Xu,Liu, Ping,Liu, Yan,Dai, Bin
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p. 709 - 715
(2018/07/14)
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- Synthesis of (E)-stilbenes and (E,E)-1,4-diphenylbuta-1,3-diene promoted by boron trifluoride-diethyl ether complex
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An efficient, simple, and practical method has been de-veloped to regioselectively synthesize (E)-stilbenes and (E,E)-1,4diphenylbuta-1,3-diene in good to excellent yields in the presence of boron trifluoride-diethyl ether complex as a catalyst in a short reaction (30-60 s) at room temperature. Georg Thieme Verlag Stuttgart.
- Narender,Papi Reddy,Madhur
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experimental part
p. 3791 - 3796
(2010/03/04)
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- Suzuki and Heck coupling reactions mediated by palladium complexes bearing trans-spanning diphosphines
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Palladium complexes of three trans-spanning diphosphines are examined for effecting C-C coupling reactions. Ten aryl halides of varying electron density were screened in Suzuki coupling reactions with phenylboronic acid and in Heck reactions with styrene.
- Smith, Rhett C.,Bodner, Christina R.,Earl, Meredith J.,Sears, Nathaniel C.,Hill, Nicholas E.,Bishop, Lee M.,Sizemore, Nicholas,Hehemann, Dave T.,Bohn, Justin J.,Protasiewicz, John D.
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p. 477 - 481
(2007/10/03)
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- Zinc metal-promoted stereoselective olefination of aldehydes and ketones with gem-dichloro compounds in the presence of chlorotrimethylsilane
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A combination of zinc metal and a catalytic amount of chlorotrimethylsilane has been found to promote the transformation of various aldehydes and ketones with gem-dichloro compounds, such as benzylidene dichloride (1a) and methyl dichloroacetate (1b), to the corresponding cross- coupling products, such as substituted styrene 3 and methyl acrylates 4 derivatives, under mild reaction conditions in THF. The E-isomer of the corresponding alkenes was obtained stereoselectively in good-to-excellent yields. The reaction serves as a very convenient one-pot procedure.
- Ishino, Yoshio,Mihara, Masatoshi,Nishihama, Shintaro,Nishiguchi, Ikuzou
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p. 2669 - 2672
(2007/10/03)
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- A highly active and stereoselective montmorillonite catalyst for arylation of conjugated alkenes
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A highly active and stereoselective heterogenised homogeneous catalyst montmorilloniteethylsilydiphenylphosphinepalladium (II) chloride complex (Pd/P is 1:1) for arylation of conjugated alkenes is reported.
- Choudary, Boyapati M.,Sarma, Ravichandra M.,Rao, Koteswara K.
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p. 719 - 726
(2007/10/02)
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- NEW SIMPLE METHOD FOR THE SYNTHESIS OF CIS-STILBENES
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A new method involving catalytic acetylenic condensation as the key stage was developed for the synthesis of cis-stilbenes.Subsequent selective hydrogenation of the synthesized alkyltolanes over Pd-CaCO3 gave a series of alkyl-substituted stilbenes. 1,8-Dimethylphenanthrene was obtained from o-iodotoluene.
- Merkushev, E. B.,Skorokhodova, T. S.
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p. 308 - 311
(2007/10/02)
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