- Synthesis of bis(halovinyl)benzenes by catalytic olefination
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Catalytic olefination of hydrazines of terephthalic and isophthalic aldehydes with polyhaloalkanes afforded the corresponding p- and m-divinylbenzene derivatives bearing halogen atoms and various functional groups at the double bonds. Stereochemical featu
- Muzalevskiy,Shikhaliev,Magerramov,Gurbanova,Geydarova,Balenkova,Shastin,Nenajdenko
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p. 678 - 682
(2014/01/23)
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- Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides
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A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright
- Liu, Liu,Wang, Yulei,Zeng, Zhiping,Xu, Pengxiang,Gao, Yuxing,Yin, Yingwu,Zhao, Yufen
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supporting information
p. 659 - 666
(2013/04/10)
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- Synthesis of dibromoolefins via a tandem ozonolysis-dibromoolefination reaction
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In this Letter we outline the synthesis of a variety of dibromoolefins (DBOs) from a series of alkenes by coupling an oxidative cleavage and a reaction with a phosphorous ylide. This approach strategically avoids isolation of reactive aldehyde intermediates and presents one of the few examples coupling carbon-carbon bond formation with ozonolysis.
- Brown, Brenna Arlyce,Veinot, Jonathan G.C.
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supporting information
p. 792 - 795
(2013/02/25)
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- Cycloaddition-based formal C-H alkynylation of isoindoles leading to the synthesis of air-stable fluorescent 1,3-dialkynylisoindoles
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Reaction of N-alkylisoindoles with (bromoethynyl)triisopropylsilane afforded 1,3-bis(triisopropylsilylethynyl) isoindoles in high yields. The formal C-H alkynylation proceeds under transition-metal-free conditions through [4 + 2] cycloaddition of the pyrrole ring of isoindole with bromoalkyne followed by ring-opening of the product.
- Ohmura, Toshimichi,Kijima, Akihito,Komori, Yusuke,Suginome, Michinori
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supporting information
p. 3510 - 3513
(2013/08/23)
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- Pd-catalyzed domino synthesis of internal alkynes using triarylbismuths as multicoupling organometallic nucleophiles
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Figure presented The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1-alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.
- Rao, Maddali L. N.,Jadhav, Deepak N.,Dasgupta, Priyabrata
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supporting information; experimental part
p. 2048 - 2051
(2010/07/03)
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- A new facile synthesis of 1,1-dibromo-2-arylethenes
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Synthetically useful 1,1-dibromo-2-arylethenes were readily prepared in good yields via double bromodesilylation of the easily accessible 1,1-bis(trimethylsilyl)-2-arylethenes using N-bromosuccinimide under mild conditions. Georg Thieme Verlag Stuttgart.
- Pawlu?, Piotr,Hreczycho, Grzegorz,Walkowiak, J?drzej,Marciniec, Bogdan
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p. 2061 - 2064
(2008/02/10)
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- One-pot conversion of activated alcohols into 1,1-dibromoalkenes and terminal alkynes using tandem oxidation processes with manganese dioxide
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Approaches to the preparation of C1-homologated dibromoalkenes and terminal alkynes from activated alcohols using one-pot tandem oxidation processes (TOPs) with manganese dioxide are outlined. The conversion of alcohols into dibromoalkenes is described using dibromomethyltriphenylphosphonium bromide and the formation of terminal alkynes was achieved via a sequential one-pot, two-step process utilising the Bestmann-Ohira reagent.
- Quesada, Ernesto,Raw, Steven A.,Reid, Mark,Roman, Estelle,Taylor, Richard J.K.
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p. 6673 - 6680
(2007/10/03)
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- Tetraarylphosphonium salts as solubility-control groups: Phosphonium-supported triphenylphosphine and azodicarboxylate reagents
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(Chemical Equation Presented) Predictable solubilities! Reagents supported on a tetraarylphosphonium group have solubilities that can be predicted. The reagents and their by-products can be readily removed, recovered, and recycled after reaction by a precipitation/filtration sequence initiated by the addition of a low-polarity solvent, such as diethyl ether. Furthermore, the supported reagents are robust and exhibit reactivities similar to their parent compounds.
- Poupon, Jean-Christophe,Boezio, Alessandro A.,Charette, Andre B.
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p. 1415 - 1420
(2007/10/03)
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- A tandem oxidation procedure for the conversion of alcohols into 1,1-dibromoalkenes
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A practical and concise route to dibromoalkenes directly from activated alcohols in good to excellent yields using a new Tandem Oxidation Procedure (TOP) is reported. We also describe the use of these dibromoalkenes as intermediates in a one-pot route to 4,5-dihydro-1H-imidazoles and in the synthesis of bromoalkynes through MTBD-induced elimination.
- Raw, Steven A.,Reid, Mark,Roman, Estelle,Taylor, Richard J. K.
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p. 819 - 822
(2007/10/03)
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- Synthesis and photophysical studies of bis-enediynes as tunable fluorophores
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We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the π-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.
- Hwang, Gil Tae,Son, Hyung Su,Ku, Ja Kang,Kim, Byeang Hyean
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p. 11241 - 11248
(2007/10/03)
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- Synthesis of highly fluorescent Y-enyne dendrimers with four and six arms
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A first generation of dendrimeric Y-enynes with extended flexible chains was synthesized using Sonogashira coupling. Dendrimers 9 and 10 are highly fluorescent in the solid state and in solution.
- Kaafarani, Bilal R.,Wex, Brigitte,Wang, Fei,Catanescu, Otilia,Chien,Neckers, Douglas C.
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p. 5377 - 5380
(2007/10/03)
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- Novel fluorophores: efficient synthesis and photophysical study.
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[structure: see text] We have synthesized novel fluorophores by using Sonogashira reactions of 1,4-bis(dibromovinyl)benzene and 2,5-bis(dibromovinyl)thiophene with various aromatic bromides. The emission maxima of these fluorophores vary from the indigo b
- Hwang,Son,Ku,Kim
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p. 2469 - 2471
(2007/10/03)
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- Reactions with Phosphinealkylenes, XXXIX. - New Methods for the Preparation of 1-Bromoacetylenes and Enynes
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1,1-Dibromoolefins 4 are obtained in good yield from the reaction of aldehydes 1 with triphenylphosphane (2) and carbon tetrabromide (3).Reaction of 4 with three moles of methylene(triphenyl)phosphorane (8) leads to the propargylidene(triphenyl)phosphoranes 11 which react with aldehydes to give the enynes 13.The ylides 11 can also prepared via the reaction of bromoacetylenes 7, which can be obtained from 4, with two moles of 8.This reaction sequence allows the synthesis of new retinoids with enyne structures from retinal.
- Bestmann, Hans Juergen,Frey, Herbert
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p. 2061 - 2071
(2007/10/02)
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