- Continuous synthesis of organozinc halides coupled to Negishi reactions
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The Negishi cross-coupling is a powerful C-C bond forming reaction. The method is less commonly used relative to other cross-coupling methods in part due to lack of availability of organozinc species. While organozinc species can be prepared, problems wit
- Alonso, Nerea,Miller, L. Zane,De M. Muoz, Juan,Alczar, Jesus,McQuade, D. Tyler
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supporting information
p. 3737 - 3741
(2015/01/16)
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- Synthesis of diarylmethanes via a Friedel-Crafts benzylation using arenes and benzyl alcohols in the presence of triphenylphosphine ditriflate
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Triphenylphosphine ditriflate (TPPD) was found to be an efficient promoter for the Friedel-Crafts benzylation of arenes with benzyl alcohols in CH 2Cl2 at room temperature. The good yields, the 1:1 molar ratio of arene and benzyl alcohol, the benzylation of chlorobenzene as a nonactivated aromatic compound at room temperature, and no by-product formation are the main advantages of this procedure.
- Khodaei, Mohammad Mehdi,Nazari, Ehsan
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experimental part
p. 5131 - 5135
(2012/09/22)
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- Selective one-pot synthesis of various phenols from diarylethanes
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Various substituted phenols were selectively synthesized by a one-pot reaction through the NHPI-catalyzed aerobic oxidation of 1,1-diarylethanes followed by treatment with dilute sulfuric acid. The Royal Society of Chemistry.
- Nakamura, Ryota,Obora, Yasushi,Ishii, Yasutaka
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supporting information; experimental part
p. 3417 - 3419
(2009/02/05)
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- Induced diastereoselectivity in photodecarboxylation of 2-phenylpropionic acid in faujasite zeolites
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Irradiation of 2-phenylpropionic acid in various cation-exchanged faujasites leads to predominant formation of dl-2,3-diphenylbutane over the meso-isomer (in marked contrast to photolysis in isotropic media) and this zeolite-induced diastereoselectivity i
- Lalitha,Pitchumani,Srinivasan
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p. 4455 - 4459
(2007/10/03)
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- Selective arylation of exocyclic N-position of 2-pyrimidylnitrenium ion photolytically generated from tetrazolo[1,5-a]pyrimidine in the presence of trifluoroacetic acid
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Photo-reactions of tetrazolo[1,5-a]pyrimidine (1) with benzene (2a) and substituted benzenes (2b-f) in the presence of trifluoroacetic acid (TFA) gave 2-(2-, 3- and 4-substituted anilino)pyrimidines (3-5) together with 2-aminopyridine (6) and biphenyl (7) or diarylmethanes (8b, 8c and 8e). From the effect of heavy-atom solvent on the reactions, it is reasonable to assume that 3-5 are formed via a singlet species, but 6-8 via a triplet species. The intermediacy of 2-pyrimidylnitrenium ion is consistent with the evidence derived by the above effect, by a Hammett plot with p = -2.9 and by effects of solvent nucleophilicity and counter-anions. The selective exocyclic N-arylation giving 3-5 is discussed.
- Takeuchi, Hiroshi,Watanabe, Keiichi
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p. 478 - 484
(2007/10/03)
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- Photodecarboxylation of 2-phenylpropionic acid in solution and included within β-cyclodextrin
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Photolysis of 2-phenylpropionic acid (1) in acetonitrile, methanol or benzene leads to ethylbenzene (2), 2,3-diphenylbutane (3d,l and meso), 1-(2-ethylphenyl)-1-phenylethane (4), 1-(4-ethylphenyl)-1-phenylethane (5) and acetophenone (6). In cyclohexane or carbon tetrachloride, solvent derived products are formed. These results involve homolytic cleavage of the C-C bond α to the carboxy group, which affords 1-phenylethyl radical (PER) as key intermediate. The α,α coupling of PER in solution to give 3 is nonstereoselective; by contrast, formation of the meso isomer is preferred upon inclusion of 1 within β-cyclodextrin. This is attributed to the coupling of two long-lived PER-CD units.
- Consuelo Jimenez,Miranda, Miguel A.,Tormos, Rosa
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p. 2953 - 2958
(2007/10/02)
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- CHLORIERENDE METHYLIERUNG VON ALDEHYD- UND KETOGRUPPEN MIT NIOB-REAGENZIEN SOWIE AUFKLAERUNG DES MECHANISMUS
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The reagents MeNbCl4 and Me2NbCl3, applied as isolated pure compounds, react with ketones in preparatively useful yields according to RR'CO -> RR'C(Cl)CH3.Whereas benzaldehyde reacts with MeNbCl4 analogously, the aliphatic aldehyde heptanal forms beside the expected product two cinechlorination products, indicating a mechanism via radicals.MeNbCl4 is highly aldehyde-vs.-ketone selective.Conversely, high ketone-vs.-aldehyde selectivity is achievable by application of MeNbCl4*PPh3 or NbCl5*PPh3 + 1.5 Me2Zn.
- Kauffmann, Thomas,Abel, Thomas,Neiteler, Gabriele,Schreer, Martin
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p. 503 - 506
(2007/10/02)
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- REACTION OF MONOSUBSTITUTED AROMATIC HYDROCARBONS WITH STYRENE
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1,1-Phenylarylethanes were obtained by the reaction of styrene with some monosubstituted aromatic hydrocarbons in the presence of titanium tetrachloride.It was established that electron-donating substituents have an effect on the yield of the arylalkylation products.
- Grushin, A. I.,Grigor'ev, V. V.,Prokof'ev, K. V.,Kozlova, N. M.
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p. 1991 - 1993
(2007/10/02)
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- The addition of simple aromatic hydrocarbons to condensed aromatic thiophenes promoted by aluminum chloride. Part II. Naphthothiophene
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The reaction of naphthothiophene with an aromatic hydrocarbon in the presence of aluminum chloride at 20 deg C gave either a 3-aryl-2,3-dihydronaphthothiophene by addition to the 2,3-bond or 2,3-dihydronaphthothiophene as a result of hydride abstraction.Occasionally 2-aryl-2,3-dihydronaphthothiophenes were obtained.At higher temperatures 2-arylnaphthothiophenes and 2,3-dihydronaphthothiophene were isolated.Attempts are made to rationalize the formation of these products in terms of protonation of naphthothiophene by moist aluminum chloride and reaction of the resulting electrophile with an aromatic substrate.
- Clark, Peter David,McKinnon, David M.
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p. 1297 - 1302
(2007/10/02)
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