- Photochemical oxidation of benzylic primary and secondary alcohols utilizing air as the oxidant
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A mild and green photochemical protocol for the oxidation of alcohols to aldehydes and ketones was developed. Utilizing thioxanthenone as the photocatalyst, molecular oxygen from air as the oxidant and cheap household lamps or sunlight as the light source, a variety of primary and secondary alcohols were converted into the corresponding aldehydes or ketones in low to excellent yields. The reaction mechanism was extensively studied.
- Nikitas, Nikolaos F.,Tzaras, Dimitrios Ioannis,Triandafillidi, Ierasia,Kokotos, Christoforos G.
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supporting information
p. 471 - 477
(2020/02/13)
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- Direct transformation of aryl 2-pyridyl esters to secondary benzylic alcohols by nickel relay catalysis
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A direct transformation of aryl esters to secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni-H species is achieved. Preliminary mechanistic studies reveal that the Ni-H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with wide functional group tolerance.
- Wu, Xianqing,Li, Xiaobin,Huang, Wenyi,Wang, Yun,Xu, Hui,Cai, Liangzhen,Qu, Jingping,Chen, Yifeng
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p. 2453 - 2458
(2019/03/29)
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- Synthesis and biological evaluation of C-3 aliphatic coumarins as vitamin K antagonists
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Since the discovery of Warfarin in the 1940s, the design of new warfarin-derived anticoagulants for rodent management has been challenging, with mainly structural modifications performed on the C3 position of the coumarin skeleton. In order to better understand the pharmacomodulation of such derivatives, we have synthesized a family of C3 (linear and branched) alkyl-4-hydroxycoumarins, which led to the identification of compounds 5e and 5f as potential short-term active anticoagulants.
- Montagut-Romans, Adrien,Boulven, Manon,Jacolot, Ma?wenn,Moebs-Sanchez, Sylvie,Hasco?t, Claire,Hammed, Abdessalem,Besse, Stéphane,Lemaire, Marc,Benoit, Etienne,Lattard, Virginie,Popowycz, Florence
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p. 1598 - 1601
(2017/03/17)
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- Rhodium-catalysed tandem hydroformylation/arylation reaction with boronic acids
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A new efficient multicatalytic process involving a single catalyst to promote tandem hydroformylation/arylation reactions is disclosed. The effect of the rhodium ligand was evaluated and the rhodium/triphenylphosphine catalytic system was selected to apply the methodology to different olefins and boronic acids. High yields (up to 89%) and good to excellent isomer ratios (up to 98:2) were achieved using aryl olefins as starting materials. This new methodology allows the preparation of secondary alcohols, from simple olefins, and paves the way for the synthesis of high-value products, namely vinylindole and anethole derivatives.
- Almeida, Ana R.,Dias, Roberto D.,Monteiro, Carlos J. P.,Abreu, Artur R.,Gois, Pedro M. P.,Bayon, J. Carles,Pereira, Mariette M.
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supporting information
p. 1223 - 1228
(2014/05/06)
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- Synthesis of new (R)-secondary carbinols with different structures via enzymatic resolution
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The present study deals with the biocatalytic enantioselective synthesis of 19 new chiral alcohols with alkyl (C11-C19) and phenyl, substituted phenyl, heteroaromatic, and naphthyl groups 4a-4z with an (R)-configuration and high enan
- Yildiz, Tuelay,Yusufolu, Aye
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experimental part
p. 1347 - 1352
(2011/11/29)
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- Lack of the neighboring group rate effect in solvolytic reactions that proceed via participation
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In order to investigate the influence of solvent polarity on the rate effect of double bonds in reactions that proceed via an extended π-participation mechanism, the solvolysis rates (kU) of the benzyl chloride derivative 1 and tertiary chlorid
- Juric, Sandra,Kronja, Olga
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p. 108 - 111
(2008/09/20)
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- Catalyzing methanolysis of alkyl halides in the interior of an amphiphilic molecular basket
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(Figure Presented) A molecular basket with four chelate units assembled on a cone-shaped calix[4]arene assumed reversed micelle-like conformation in 5% methanol/carbon tetrachloride. The inwardly facing hydroxyl groups on the chelates concentrated the pol
- Ryu, Eui-Hyun,Cho, HongKwan,Zhao, Yan
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p. 5147 - 5150
(2008/09/17)
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- Crenulacetal C, a marine diterpene, and its synthetic mimics inhibiting Polydora websterii, a harmful lugworm damaging pearl cultivation
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Polydora websterii, a harmful lugworm that has serious adverse effects on pearl oyster cultivation, was inhibited by a marine diterpene, crenulacetal C, isolated from the brown alga Dictyota dichotoma. Based on consideration of the activity-structure relationship, several synthetic compounds having an aromatic moiety with a hydroxyalkyl chain were prepared. Bioassay using larvae of Polydora websterii as well as pearl oysters (Pinctada fucata martians) suggested that 1-(2-ferrule)-1-nonanol was the most promising inhibitor.
- Takikawa, Mami,Uno, Kiyoko,Ooi, Takashi,Kusumi, Takenori,Akera, Shusaku,Muramatsu, Morimitsu,Mega, Hirohiko,Horita, Chie
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p. 462 - 466
(2007/10/03)
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- Preparation of Alkylchromium Reagents by Reduction of Alkyl Halides with Chromium(II) Chloride under Cobalt Catalysis
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Alkyl halides and tosylates are reduced with CrCl2 in the presence of a catalytic amount of vitamin B12 or cobalt phthalocyanine to give alkylchromium reagents, which add to aldehydes without affecting the coexisting ketone or ester groups.
- Takai, Kazuhiko,Nitta, Kenji,Fujimura, Osamu,Utimoto, Kiitiro
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p. 4732 - 4734
(2007/10/02)
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- Rates and Alkyl Group Size in Solvolysis of Alkyl Derivatives
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The logarithm of solvolysis rate constants in 80percent aqueous ethanol of 1,1-dimethyl-1-alkyl chlorides 1 and 1-phenyl-1-alkyl chlorides 2 decrease monotonically with increasing number of carbon atoms in the alkyl group.The first member of both series deviates from the corresponding correlation lines which have the some slope.In contrast, solvolysis rates in 80percent aqueous ethanol of 1-methyl-1-alkyl tosylates 3 do not depend upon the size of the alkyl group.The results are rationalized in terms of a mechanism that is very similar in reactions of series 1 and 2 but different from that of series 3.
- Orlovic, Mirko,Kronja, Olga,Humski, Kresimir,Borcic, Stanko,Polla, Eugenio
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p. 3253 - 3256
(2007/10/02)
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