- Preparation of dialkoxyborylbis(bromozincio)methane and its reaction with electrophiles
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Dialkoxyborylbis(bromozincio)methane was prepared from dialkoxyboryldibromomethane by the Pb-catalyzed reaction with zinc. The dialkoxyborylbis(bromozincio)methane afforded vinylboranes by TiCl4-mediated reaction with aldehydes or ketones. The
- Matsubara, Seijiro,Otake, Yasuyuki,Hashimoto, Yuko,Utimoto, Kiitiro
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- Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant
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Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.
- Zhou, Xibing,Zhang, Guoying,Huang, Renbin,Huang, Hanmin
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p. 365 - 369
(2021/01/26)
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- Single electron transfer-induced Grignard cross-coupling involving ion radicals as exclusive intermediates
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The mechanism of the previously developed cross-coupling reaction of aryl Grignard reagents with aryl halides was explored in more detail. Single electron transfer from an aryl Grignard reagent to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle consists entirely of anion radical intermediates.
- Uchiyama, Nanase,Shirakawa, Eiji,Hayashi, Tamio
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supporting information
p. 364 - 366
(2013/02/23)
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- Palladium-catalyzed cross-coupling reactions of organogold(i) phosphanes with allylic electrophiles
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Aryl and alkenylgold(i) phosphanes react regioselectively with allylic electrophiles such as cinnamyl and geranyl halides (bromide, chloride and acetates) under palladium catalysis in THF at 80 °C to afford the α-substitution product with moderate to high yields. When the reaction is performed with a chiral enantiopure secondary acetate, the α-substituted cross-coupling product is obtained with complete inversion of the stereochemistry.
- Pena-Lopez, Miguel,Ayan-Varela, Miguel,Sarandeses, Luis A.,Sestelo, Jose Perez
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experimental part
p. 1686 - 1694
(2012/03/22)
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- Mild TiIII- and Mn/ZrIV-catalytic reductive coupling of allylic halides: Efficient synthesis of symmetric terpenes
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(Chemical Equation Presented) Two new efficient methods for the regioselective homocoupling of allylic halides using either catalytic Ti III or the combination Mn/ZrIV catalyst have been developed. The regio- and stereoselectivity of the process proved to increase significantly when the Mn/ZrIV catalyst is used as the coupling reagent and when cyclic substituted allylic halides are used as substrates. The use of Lewis acids such as collidine hydrochloride allowed the quantity of catalyst to be lowered up to 0.05 equiv. We have proved the utility of these protocols with the synthesis of different terpenoids such as (+)-β-onoceradiene (1), (+)-β-onocerine (2), squalene (5), and advanced key-intermediates in the syntheses of (+)-cymbodiacetal (3) and dimeric ent-kauranoids as xindongnin M (4a).
- Barrero, Alejandro F.,Herrador, M. Mar,Quilez Del Moral, Jose F.,Arteaga, Pilar,Arteaga, Jesus F.,Dieguez, Horacio R.,Sanchez, Elena M.
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p. 2988 - 2995
(2007/10/03)
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- Manganese- or iron-catalyzed homocoupling of grignard reagents using atmospheric oxygen as an oxidant
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Atmospheric oxygen was used for the first time as an oxidant in metal-catalyzed homocoupling of Grignard reagents. These manganese- or iron-catalyzed reactions are efficient, cheap, and eco-friendly. They are applicable to the large-scale synthesis of symmetrical conjugated compounds. Copyright
- Cahiez, Gerard,Moyeux, Alban,Buendia, Julien,Duplais, Christophe
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p. 13788 - 13789
(2008/04/11)
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- Copper catalyzed oxidation of organozinc halides
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A wide range of organozinc substrates may be oxidized in the presence of catalytic copper to give carbon-carbon bonds in high yield. The Royal Society of Chemistry 2006.
- Su, Xianbin,Fox, David J.,Blackwell, David T.,Tanaka, Kiyotaka,Spring, David R.
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p. 3883 - 3885
(2007/10/03)
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- Reductive coupling of allylic esters with carbonyl compounds mediated by the mischmetall/[SmI2/Pd0cat.′] cat. system
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The mischmetall/[SmI2/Pd0cat.′] cat. system has been used to mediate the allylation of ketones using a variety of allylic esters (acetates, carbonates and phosphates). Thus, a "two-stage catalysis" has been carried out using SmI2 and Pd(PPh3)4 in catalytic amounts together with mischmetall (an alloy of the light lanthanides) as a co-reductant. A catalytic scheme that takes into account previously reported reactions of SmI2/Pd 0cat. and mischmetall/SmI2,Cat. systems is proposed. It has also been shown that palladium complexes catalyse the addition of organolanthanide species to ketones. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Medegan, Sedami,Helion, Florence,Namy, Jean-Louis
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p. 4715 - 4722
(2007/10/03)
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- Et3B-Pd-promoted allylation of benzaldehyde with allylic alcohols
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In the presence of Pd(OAc)2 (0.05 equiv.) and PPh3 (0.1 equiv.), triethylborane promotes a variety of allyl alcohols to undergo allylation of benzaldehyde to provide homoallyl alcohols in good yield. (C) 2000 Elsevier Science Ltd.
- Kimura, Masanari,Tomizawa, Tatsuya,Horino, Yoshikazu,Tanaka, Shuji,Tamaru, Yoshinao
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p. 3627 - 3629
(2007/10/03)
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- Allylation of aldehydes via Umpolung of π-allylpalladium(II) with triethylborane
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Triethylborane induces allylic substrates (benzoates, phenyl ethers, benzyl ethers, but not halides) to undergo allylation of aldehydes in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(O). The reaction proceeds via Umpolung o
- Kimura, Masanari,Kiyama, Iku,Tomizawa, Tatsuya,Horino, Yoshikazu,Tanaka, Shuji,Tamaru, Yoshinao
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p. 6795 - 6798
(2007/10/03)
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- Palladium( 0) -catalyzed phenoxycarbonylation of allylic carbonates
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Phenoxycarbonylation of various allylic carbonates under various conditions in tetrahydrofuran is described. The nature and ratio of the products formed are dependent on the presence of water, carbon monoxide pressure and addition of various inorganic halides. The formation of a product arising from dimerization of the allylic carbonate is discussed.
- Goux, Catherine,Lhoste, Paul,Sinou, Denis,Masdeu, Anna
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p. 139 - 143
(2007/10/03)
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- Palladium-catalyzed cross-coupling of allylic carbonates with alkenylfluorosilanes in the absence of fluoride ion
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Alkenylfluorosilanes smoothly underwent cross-coupling reaction with allylic carbonates in the presence of a palladium catalyst and in the absence of fluoride ion to give 1,4-dienes in good yields with retention of configuration.
- Matsuhashi, Hayao,Hatanaka, Yasuo,Kuroboshi, Manabu,Hiyama, Tamejiro
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p. 1539 - 1540
(2007/10/02)
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- Regio- and Stereoselective Synthesis of 1,5-Dienes Using Allylic Barium Reagents
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The highly α,α' selective and sterocontrolled homocoupling reaction of allylic halides was achieved using barium reagent.The double-bond geometry of the starting allylic chloride was completely retained.The α,α' cross-coupling products were also prepared stereospecifically and regioselectively by this method.
- Yanagisawa, Akira,Hibino, Hiroaki,Habaue, Shigeki,Hisada, Yoshiyuki,Yasue, Katsutaka,Yamamoto, Hisashi
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p. 1263 - 1268
(2007/10/03)
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- Selective Alkylation and Allylation of Allylic Halides by Tetraorganoidates: Regio- and Stereo-selective Synthesis of Rosefuran and Sesquirosefuran
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Tetraalkylindanes regioselectively alkylate allylic bromides at the α-carbon.In this way, 1,5-dienes have been regio- and stereo-selectively synthesized by the allyl-allyl coupling of allylic bromides and allylic indates, including rosefuran 1 and sequirosefuran 3.
- Araki, Shuki,Jin, Shun-Ji,Butsugan, Yasuo
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p. 549 - 552
(2007/10/02)
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- Zinc Mediated Allylation of Aldehydes and Ketones with Cinnamyl Chloride in Aqueous Medium
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The Zn mediated reactions of cinnamyl chloride with aldehydes and ketones in THF-NH4Cl(aq) give-besides α- and γ-addition products-phenyl propenes and dicinnamyls, indicating the presence of radical intermediates in the reaction.
- Sjoeholm, Rainer,Rairama, Riitta,Ahonen, Matthias
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p. 1217 - 1218
(2007/10/02)
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- Versatile Desilylative Cross-Coupling of Silyl Enol Ethers and Allylic Silanes via Oxovanadium-Induced Chemoselective One-Electron Oxidation
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The chemoselective cross-coupling of silyl enol ethers and allylic silanes to γ,δ-unsaturated ketones is achieved by the oxovanadium(V)-induced oxidative desilylation of the more readily oxidizable organosilicon compounds.
- Hirao, Toshikazu,Fujii, Takashi,Ohshiro, Yoshiki
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p. 10207 - 10214
(2007/10/02)
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- Perturbation of the degenerate, concerted cope rearrangement by two phenyl groups in "active" positions of (E)-1,4-diphenylhexa-1,5-diene. Acceleration by high pressure as criterion of cyclic transition states
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Previous examinations of radical-stabilizing substituents in the two distinct types of position in the hypothetical "aromatic" transition state of the thermal Cope rearrangement, designated "a" or active and "n" or nodal after the allyl radical have concentrated on their effect in the "n" positions. In order to provide a quantitatively reliable reference for the "a" position, the activation parameters of the degenerate rearrangement of (6-13C)-1,4-diphenylhexa-1,5-diene have been evaluated: Ea = 30.8 ± 0.4 kcal/mol; log A = 10.14 ± 0.2. The soundly energetically-based proposition that these observations relate to a concerted mechanism is strongly supported by the observation of a 3.0-fold increase in rate of approach to equilibrium on increasing the pressure from 1 bar to 6000 bar (162°C; benzene-d6). This rearrangement like that of cis-1,2-divinylcyclobutane and rac- and meso-3,4-diphenylhexa-1,5-diene, has a negative volume of activation. In contrast, trans-1,2-divinylcyclobutane, which does not rearrange by a cyclic transition state and gives cycloocta-1,5-diene, 4-vinylcyclohexene, and butadiene as products, has a positive volume of activation. To place the possibility of reaction by the homolytic/colligative (dissociative/recombinative) mechanism on a "quantitative" base, a further sighting on the heat of formation of the cinnamyl radical is provided by activation parameters for thermal syn-anti equilibration between (E)- and (Z)-1,1′-bi-3-phenylcyclohex-2-enylidene: Ea = 35.8 ± 0.2 kcal/mol; log A = 12.7 ± 0.1. After correction for conjugative interaction between phenyl and the double bond in the educts and without regard for any proposed structure for the transition state, the two phenyl groups in "a" positions appear to have lowered the enthalpy of activation by 7.7 kcal/mol relative to the paradigm, hexa-1,5-diene, whereas the two phenyl groups in the "n" positions of 3,5-diphenylhexa-1,5-diene have lowered the enthalpy of activation by 17.0 kcal/mol.
- Doering,Birladeanu, Ludmila,Sarma, Keshab,Teles, Joaquim Henrique,Kl?rner,Gehrke, Jan-Stephan
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p. 4289 - 4297
(2007/10/02)
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- Oxovanadium-induced oxidative desilylation of allylic and benzylic silanes
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Cinnamyltrimethylsilane underwent desilylation via one-electron oxidation with VO(OEt)Cl2, which was applied to the cross-coupling with the less oxidizable allylic silanes to give the corresponding 1,5-hexadienes. Chlorination or aromatization
- Fujii, Takashi,Hirao, Toshikazu,Ohshiro, Yoshiki
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p. 5601 - 5604
(2007/10/02)
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- Synthesis and reaction of (η5-pentamethylcyclopentadienyl)bis(allyl)tantalum(III) complexes; crystal structure of Ta(η5-C5Me5)(η3-1-phenylallyl)2
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We report here the synthesis and X-ray structure of a mononuclear 16-electron (η5-pentamethylcyclopentadienyl)bis(allyl)-tantalum complex, Cp*Ta(η3-PhC3H4)2 (2).Carbonylation of 2 induced the coupling reaction with phenylallyl groups bound to tantalum to give 1,6-diphenyl-1,5-hexadiene and carbonyltantalum complexes.Oxidation of 2 with one-electron oxidants, DDQ and TCNQ, gave the tantalum(IV) complexes, *Ta(PhC3H4)2>.
- Mashima, Kazushi,Yamanaka, Yoshimichi,Gohro, Yoshihiko,Nakamura, Akira
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- On the Regioselectivity of Coupling of Substituted Allyl Radicals. Steric Versus FMO Control
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The photo-induced decomposition of substituted-homoallylic 4-nitrobenzenesulfenates produces substituted allyl radicals which undergo dimerization and coupling with the 4-nitrobenzenethiyl radical.The regioselectivity of the dimerization of the allyl redi
- Pasto, Daniel J.,L'Hermine, Gael
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p. 3259 - 3272
(2007/10/02)
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- Palladium-Catalyzed, Atmospheric Pressure Carbonylation of Allylic Halides under the Influence of Sodium Hydroxide or Alkoxides. A Facile Synthesis of β,γ-Unsaturated Acids
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The palladium-catalyzed, atmospheric-pressure carboxylation of allylic halides occurs readily in an aqueous sodium hydroxide/organic solvents two-phase system, giving β,γ-unsaturated acids.Phosphine complexes (I, L=m-(Ph2P)C6H4SO3Na; II, L=Ph3P) or Na2 (III) can be used as the catalyst.Atmospheric-pressure alkoxycarbonylation is realized under the influence of a homogeneous alcoholic solution of sodium alkoxide.Phosphine-free palladium complexes, such as 2 or III, are the favored catalyst. β,γ-Unsaturated esters are obtained in high yields.
- Okano, Tamon,Okabe, Nobuyuki,Kiji, Jitsuo
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p. 2589 - 2593
(2007/10/02)
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- PALLADIUM-CATALYZED REACTION OF 3-BROMOINDOLE DERIVATIVE WITH ALLYL ESTERS IN THE PRESENCE OF HEXA-n-BUTYLDISTANNANE
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The palladium-catalyzed cross-coupling reaction of ethyl 3-bromo-1-tosylindole-2-carboxylate (9) with a variety of substituted allylic acetates or carbonates (10) in the presence of hexa-n-butyldistannane (6) gave 3-allylated indoles (11) in high yields.
- Yokoyama, Yuusaku,Ikeda, Masato,Saito, Masaaki,Yoda, Tomoko,Suzuki, Hideharu,Murakami, Yasuoki
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p. 1505 - 1511
(2007/10/02)
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- Palladium-Catalyzed, Atmospheric Pressure Carbonylation of Allylic Chlorides in Two-Phase Aqueous Sodium Hydroxide-Organic Solvent Media
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The palladium-catalyzed, atmospheric pressure carbonylation of allylic chlorides is realized in aqueous NaOH/benzene.Phosphine complexes PdCl2L2 (I) (a, L=Ph2P(m-C6H4SO3Na; b, L=Ph3P), or Na2PdCl4 can be used as the catalyst.
- Kiji, Jitsuo,Okano, Tamon,Nishiumi, Wataru,Konishi, Hisatoshi
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p. 957 - 960
(2007/10/02)
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- REACTIONS OF ?-ALLYL COMPLEXES OF Ti(III) WITH ALLYL, ALKYL, AND PROPARGYL ELECTROPHILES
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The reactions of the ?-allyl complexes of Ti(III) with allyl bromides lead to the production of a mixture of cross-coupling and homocoupling products.In the case of alkyl and propargyl halides the dehalogenation products are formed.The reaction of the ?-allyl complexes of Ti(III) with allyl acetates, allyl phenyl ethers, and allyl aryl sulfones are catalyzed by Pd(PPh3)4 and give cross-coupling or elimination products, depending on the structure of the initial substrate.
- Kasatkin, A. N.,Kulak, A. N.,Tolstikov, G. A.,Lomakina, S. I.
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p. 1875 - 1889
(2007/10/02)
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- An Efficient Electrochemical Coupling of Allylic Halides by Using a Copper Anode
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A new electrolytic method for an efficient coupling of allylic halides by the use of a copper anode and a platinum cathode in the precence of sodium iodide is described.A method which avoids a loss of the copper anode owing to dissolution is also described.
- Tokuda, Masao,Endate, Kazuhiro,Suginome, Hiroshi
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p. 945 - 948
(2007/10/02)
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- Reaction of Phenyl-Substituted Allyllithiums with tert-Alkyl Bromides. Remarkable Difference in the Alkylation Regiochemistry between a Polar Process and the One Involving Single-Electron Transfer
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The reaction of phenyl-substituted allyllithiums 1a-h with tert-alkyl bromides was investigated systematically.The alkylation regiochemistry was influenced in a complicated fashion by various factors including substituent effects, both steric and electronic, solvents, and the presence of strongly coordinating additives, tetramethylethylenediamine and hexamethylphosphoramide.On the basis of the cyclizable probe experiments, the observed regiochemistry was interpreted as follows. (a) The reaction proceeds by two alternative pathways, a polar one and single electron transfer (SET), the extent of each path being influenced by the variable factors and (b) a polar pathway favors coupling at the phenyl-substituted site (C-1), while in the case of SET the C-C bond formation occurs predominantly at the site far from the phenyl substituent (C-3).
- Tanaka, Jiro,Nojima, Masatomo,Kusabayashi, Shigekazu
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p. 3391 - 3397
(2007/10/02)
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- Hexacarbonylmolybdenum(0)-Catalyzed Reductive Coupling of Allylic Acetates
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The reaction of allylic acetates with zinc in the presence of a catalytic amount of hexacarbonylmolybdenum(0) led to reductive coupling for the formation of a 1,5-diene framework.Reductive coupling of nerolidyl acetate provided squalene and its isomers in high yield.
- Masuyama, Yoshiro,Otake, Kiyotaka,Kurusu, Yasuhiko
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p. 1527 - 1528
(2007/10/02)
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- Reductive Dimerization of Allyl and Benzyl Halides in Pb/n-Bu4NBr-DMF and PbBr2/Al-DMF Systems
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Reductive dimerization of allyl and benzyl halides has been performed by treatment with Pb/n-Bu4NBr and catalytic PbBr2/Al in N,N-dimethylformamide.
- Tanaka, Hideo,Yamashita, Shiro,Toru, Sigeru
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p. 1951 - 1953
(2007/10/02)
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- Reaction of 1-Arylpropenyl-lithium with t-Alkyl Bromides. The Influence of Substituent Electronic Effects and Additives on the Course of the Reaction
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The reaction of 1-arylpropenyl-lithium (1a-c) with t-alkyl bromides proceeds by either a nucleophilic substitution or single electron transfer mechanism, the preferred pathway being a function of electronic substituent effects and the absence or presence of tetramethylethylenediamine or hexamethylphosphoramide.
- Tanaka, Jiro,Nojima, Masatomo,Kusabayashi, Shigekazu
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p. 242 - 244
(2007/10/02)
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- Reaction of 1-Aryl-3-chloropropenes with Grignard Reagents. Nucleophilic Substitution versus Single-electron Transfer
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The reactions of ambident 1-aryl-3-chloropropenes (1a-e) with a series of Grignard reagents, R'MgY (R' = Me, Pr, Ph, Pri, But; Y = Br, I), were carried out in diethyl ether (EE) and tetrahydrofuran (THF).The products were a mixture of two alkylation products (2) and (3), and three dimerization products (4)-(6).The alkylation:dimerization ratio and the composition of the two alkylation products were a marked function of substituent electronic effects in the chlorides (1a-e), R' or Y of R'MgY, and solvent.On the basis of the stereochemistry of alkylation, cyclizable probe experiments, and the effect of the addition of FeCl3 on product composition, the following conclusions were obtained.First, dimers (4)-(6) are most likely to be produced by a mechanism involving single-electron transfer (SET).Second, for the formation of alkylation products (2) and (3), three alternative pathways contribute depending on the nature of R'MgY and solvent, (a) competitive SN2-SN2' pathways in the reaction of R'MgBr in EE, (b) a process involving SET in the reaction with R'MgI in EE, and (c) SN2 pathways in the reaction of R'MgBr in THF.
- Muraoka, Kiyoshige,Nojima, Masatomo,Kusabayashi, Shigekazu,Nagase, Shigeru
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p. 761 - 768
(2007/10/02)
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- PALLADIUM-CATALYZED COUPLING OF ELECTROGENERATED ALLYLTIN REAGENTS
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Palladium-catalyzed homocoupling of allylic halides and acetates under in situ electrochemical generation of the allyltin reagent was developed.
- Yoshida, Jun-ichi,Funahashi, Hirokatsu,Iwasaki, Hiroya,Kawabata, Nariyoshi
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p. 4469 - 4472
(2007/10/02)
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- PALLADIUM-CATALYZED COUPLING OF ALLYLIC ACETATES WITH ZINC
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Allylic acetates were coupled with zinc dust in the presence of a catalytic amount of to give the corresponding 1,5-dienes under mild conditions in high yields.Significant cosolvent effects were found with methanol or 1,2-ethanediol in tetrahydrofuran.
- Sasaoka, Shin-ichi,Yamamoto, Taku,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
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p. 315 - 318
(2007/10/02)
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- New Method for Coupling Allylic Halides: Use of Te2- Species
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A variety of allylic halides were treated with Te2- (generated in situ) to afford coupled 1,5-dienes (average yield 78percent for 11 examples).Mechanistic studies establish that bisallylic tellurides are produced, and these decompose into allylic radicals which then dimerize.
- Clive, Derrick L.J.,Anderson, Paul C.,Moss, Neil,Singh, Alok
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p. 1641 - 1647
(2007/10/02)
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- Stereochemistry of Addition of Allylic Grignard Reagents to 3-(Hydroxymethyl)cyclopropenes
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Allylic Grignard reagents add to the double bonds of alkyl-substituted 3-(hydroxymethyl)cyclopropenes.In the products, both the allyl group and the group (H or CO2H) replacing magnesium are cis to the hydroxymethyl group.The new carbon-carbon bond is formed preferentially at the more substituted allylic carbon of the allyl group and at the more substituted carbon of the cyclopropene double bond.
- Richey, Herman G.,Bension, Rouvain M.
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p. 5036 - 5042
(2007/10/02)
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- Electro-organic Reactions. Part 16. The Preparative-scale Cathodic Hydrogenolysis and Coupling of Benzyl-, Allyl-, Cinnamyl-, and Polyenylphosphonium salts
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An investigation of the cathodic reduction of benzyltriphenylphosphonium nitrate confirms that optimum yields of the product of coupling (bibenzyl) are formed at an aluminium cathode using high current densities and in dimethylformamide or hexamethylphosphoramide solution.The cathodic reduction of allylphosphonium salts gives mainly cleavage; e.g. α-farnesene (5) is obtained in 32percent yield from the corresponding farnesylphosphonium salt.Moderately efficient coupling (ca. 30percent) is observed for the electro-reduction of trans-cinnamyltriphenylphosphonium nitrate (6) and a C15 polyenylphosphonium salt (7).The products of coupling have been fully characterised; the relative proportions of positional isomers are apparently dictated by steric factors.
- Utley, James H. P.,Webber, Andrew
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p. 1154 - 1160
(2007/10/02)
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- ALLYLSTANNANES AS ELECTROFUGAL PARTNERS IN ALLYLIC ALKYLATION
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Unsymmetrical allyl-allyl couplings occur between allylstannanes and allyl acetates catalyzed by palladium(0) and a novel direct coupling of an allyl acetate in the presence of a distannane and a palladium(0) catalyst is also possible.
- Trost, Barry M.,Keinan, Ehud
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p. 2595 - 2598
(2007/10/02)
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