1560-96-9Relevant academic research and scientific papers
Large-scale synthesis of immunoactivating natural product, pristane, by continuous microfluidic dehydration as the key step
Tanaka, Katsunori,Motomatsu, Shinya,Koyama, Koichi,Tanaka, Shin-Ichi,Fukase, Koichi
, p. 299 - 302 (2007)
(Figure Presented) An efficient protocol of dehydration was developed under microfluidic conditions. The method was applied to a multikilogram synthesis of pristane, a biologically important natural product, which is now widely used as an adjuvant for monoclonal antibody production.
Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings
Bernauer, Josef,Wu, Guojiao,Von Wangelin, Axel
, p. 31217 - 31223 (2019/10/19)
An iron-catalysed allylation of organomagnesium reagents (alkyl, aryl) with simple allyl acetates proceeds under mild conditions (Fe(OAc)2 or Fe(acac)2, Et2O, r.t.) to furnish various alkene and styrene derivatives. Mechanistic studies indicate the operation of a homotopic catalyst. The sequential combination of such iron-catalysed allylation with an iron-catalysed hydrogenation results in overall C(sp3)-C(sp3)-bond formation that constitutes an attractive alternative to challenging direct cross-coupling protocols with alkyl halides.
Iron-catalyzed AlkylAlkyl negishi coupling of organoaluminum reagents
Agata, Ryosuke,Kawamura, Shintaro,Isozaki, Katsuhiro,Nakamura, Masaharu
supporting information, p. 238 - 241 (2019/03/13)
The first iron-catalyzed cross-coupling reaction of alkyl halides with alkylaluminum reagents (alkylalkyl Negishi coupling) is developed using an iron/bisphosphine catalyst system. The reaction shows high functional group tolerance: various primary alkyl halides possessing a non-protected indole, carboxyl, or hydroxy group are coupled with primary alkylaluminum reagents in good yields. Potassium fluoride plays a key role to promote the reaction by generating an aluminate species, which facilitates the transmetalation between the organoaluminum and the iron catalyst.
Photoinduced Charge-Transfer State of 4-Carbazolyl-3-(trifluoromethyl)benzoic Acid: Photophysical Property and Application to Reduction of Carbon?Halogen Bonds as a Sensitizer
Matsubara, Ryosuke,Shimada, Toshiyuki,Kobori, Yasuhiro,Yabuta, Tatsushi,Osakai, Toshiyuki,Hayashi, Masahiko
supporting information, p. 2006 - 2010 (2016/07/28)
The photoinduced persistent intramolecular charge-transfer state of 4-carbazolyl-3-(trifluoromethyl)benzoic acid was confirmed. It showed a higher catalytic activity in terms of yield and selectivity in the photochemical reduction of alkyl halides compared to the parent carbazole. Even unactivated primary alkyl bromides could be reduced by this photocatalyst. The high catalytic activity is rationalized by considering the slower backward single-electron transfer owing to the spatial separation of the donor and acceptor subunits.
Process for hydrogenation of carboxylic acids and derivatives to hydrocarbons
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Page/Page column 7-8, (2008/06/13)
A process for hydrogenating a carboxylic acid and/or derivative thereof having a carboxylate group represented by the general formula R1COO-, which process comprises feeding hydrogen and the carboxylic acid and/or derivative thereof to a reactor and maintaining conditions within the reactor such that hydrogen reacts with the carboxylic acid and/or derivative thereof to produce a product stream comprising carbon dioxide, carbon monoxide, methane and hydrocarbons represented by general formulae R1H and R1CH3, characterised in that the molar ratio of R1H : R1CH3 is above a pre-determined value and/or the mole ratio of the sum of carbon dioxide, carbon monoxide and methane to carboxylate groups is above a pre-determined value.
A Facile Method for Synthesis of Alkyl Phenyl Selenides. The Reaction of Diphenyl Diselenide with Oxygen-containing Compounds Using La/Me 3SiCl/cat.I2/cat.CuI System
Nishino, Toshiki,Nishiyama, Yutaka,Sonoda, Noboru
, p. 918 - 919 (2007/10/03)
Alcohols, ethers, and esters were directly converted to the corresponding alkyl phenyl selenides by the reaction of diphenyl diselenide and the La/Me 3SiCl/cat.I2/cat.CuI. It was suggested that alkyl phenyl sele
Deoxygenative dimerization of benzylic and allylic alcohols, and their ethers and esters using lanthanum metal and chlorotrimethylsilane in the presence of a catalytic amount of iodine and copper(I) iodide
Nishino, Toshiki,Nishiyama, Yutaka,Sonoda, Noboru
, p. 635 - 641 (2007/10/03)
Benzylic and allylic alcohols were deoxygenatively dimerized by a treatment with lanthanum metal and chlorotri-methylsilane in the presence of a catalytic amount of iodine, giving the corresponding coupling products, alkanes, in moderate-to-good yields. This dimerization reaction was dramatically accelerated by the addition of a catalytic amount of copper(I) iodide. Similarly, ethers and esters were deoxygenatively dimerized by La/Me3SiCl/cat.I2/cat.CuI system in the presence of a catalytic amount of H2O.
Reduction of organic halides with lanthanum metal: A novel generation method of alkyl radicals
Nishino, Toshiki,Watanabe, Toshihisa,Okada, Mitsuo,Nishiyama, Yutaka,Sonoda, Noboru
, p. 966 - 969 (2007/10/03)
Results of the reaction of alkyl halides with lanthanum metal have been shown. The reduction of alkyl iodide with 1/3 equiv of lanthanum metal efficiently proceeded to give the corresponding reductive dimerized products along with the formation of reduction and dehydroiodination products. In the case of alkyl bromides and chlorides, the reaction did not proceed under the same reaction conditions as that of alkyl iodides; however, the reaction was dramatically promoted by the addition of a catalytic amount of iodine. A reaction pathway including alkyl radicals was suggested.
Reaction of Raney Nickel with Alcohols
Krafft, Marie E.,Crooks, William J.,Zorc, Branka,Milczanowski, Stephen E.
, p. 3158 - 3163 (2007/10/02)
The reaction of Raney nickel with a variety of functional groups was studied.Ethers, esters, and alkyl chlorides were found to be stable to Raney nickel in refluxing toluene; however, alcohols were found to be reactive.Primary alcohols were oxidized to aldehydes and the subsequently decarbonylated, secondary alcohols were oxidized to the corresponding ketone, and tertiary alcohols were deoxygenated.
