3508-00-7Relevant academic research and scientific papers
Catalytic Access to Alkyl Bromides, Chlorides and Iodides via Visible Light-Promoted Decarboxylative Halogenation
Candish, Lisa,Standley, Eric A.,Gómez-Suárez, Adrián,Mukherjee, Satobhisha,Glorius, Frank
supporting information, p. 9971 - 9974 (2016/07/19)
Herein is reported the catalytic, visible light-promoted, decarboxylative halogenation (bromination, chlorination, and iodination) of aliphatic carboxylic acids. This operationally-simple reaction tolerates a range of functional groups, proceeds at room temperature, and is redox neutral. By employing an iridium photocatalyst in concert with a halogen atom source, the use of stoichiometric metals such as silver, mercury, thallium, and lead can be circumvented. This reaction grants access to valuable synthetic building blocks from the large pool of cheap, readily available carboxylic acids.
Light-mediated deoxygenation of alcohols with a dimeric gold catalyst
McCallum, Terry,Slavko, Ekaterina,Morin, Mathieu,Barriault, Louis
supporting information, p. 81 - 85 (2015/02/18)
A new protocol for the reductive deoxygenation of primary alcohols was explored. This photo-mediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au2(dppm)2]Cl2 [dppm = 1,1-bis(diphenylphosphino)methane] as a photoredox catalyst. The highly efficient methods discussed are marked by the use of UVA light-emitting diodes, which have significantly reduced reaction times and lowered setup cost.
Synthesis of [14C] acids from their unlabeled counterparts and application toward a novel [14C] labeled hepatitis C virus polymerase inhibitor
Ho, Jonathan Z.,Wallace, Michael A.,Tang, Yui S.,Zhang, Andy S.,Braun, Matthew P.
, p. 251 - 253 (2011/05/02)
A strategy has been developed for the rapid construction of a [ 14C] acid from either an aromatic or an alkyl acid via a decarboxylation-carboxylation sequence. A [14C] labeled heptatitis C virus polymerase inhibitor was prepared. Other examples and the limitations of this methodology are discussed. Copyright
Synthesis of racemic and each enantiomer of 3-methylnonacosanol, a new plant growth regulator from Lowsonia inermis
Kulkarni, Bheemashankar A.,Sankaranarayanan, Sivaraman,Subbaraman, Ayalur S.,Chattopadhyay, Subrata
, p. 1571 - 1577 (2007/10/03)
An efficient synthesis of the title compound I in racemic and enantiomeric forms has been developed starting from 10-undecenoic acid. For the enantiomeric synthesis, a lipase catalyzed acylation strategy was employed to prepare the required methyl branched chiron which was subsequently derivatized to give the enantiomers of I. The plant growth regulatory (PGR) assay of I, carried out with hypocotyl cuttings of French beans (Phaseolus vulgaris L.) in Steinberg's nutrient medium revealed appreciable activity at a concentration of 2.5 ppm. The PGR activities of the compound both in racemic and enantiomeric forms were better than 1- triacontanol, the enantiomer, (S)-I being the best test candidate.
A further synthesis of an analogue of the antifungal/antiherbivore lipid from avocado
Carman, Raymond M.,Karoli, Tomislav
, p. 955 - 959 (2007/10/03)
A further synthesis of the saturated racemic derivative (1b) of the avocado diene (1a) ((R,Z,Z)-2-hydroxy-4-oxohenicosa-12,15-dien-l-yl acetate; 'persin') is described.
Novel antifeedant and insecticidal compounds from avocado idioblast cell oil
Rodriguez-Saona, Cesar,Millar, Jocelyn G.,Maynard, David F.,Trumble, John T.
, p. 867 - 889 (2007/10/03)
Several insecticidal compounds have been identified by bioassaydriven fractionation of avocado, Persea americana Mill, idioblast cell oil. A flash chromatography fraction of the oil showed substantial toxicity to early instars of the generalist insect herbivore, Spodoptera exigua (Hubner) (100% mortality after seven days). Following further fractionation, five biologically active compounds, 2-(pentadecyl)furan, 2-(heptadecyl)furan, 2-(1E-pentadecenyl)furan, 2-(8Z, 11Z-heptadecadienyl)furan, and the triglyceride triolein, were identified. Several minor components were also tentatively identified, including 2-(1Z-pentadecenyl)furan, 2-(1E-heptadecenyl)furan, and 2-(1E,8Z, 11Z-heptadecatrienyl)furan. Several 2-alkylfurans of this type have been reported previously from avocado (Persea spp.) and have received the common name of avocadofurans. The major compounds were tested individually for toxic and growth inhibitory effects. Individually, the compounds had low to moderate toxicity. Of these, 2-(pentadecyl)furan had the greatest effects, with an LC50 value of 1031 μg/g. At concentrations of 600 μg/g or higher in diets, larval growth was inhibited by >70% compared to controls. The analogous 2-(heptadecyl)furan had an LC50 value of 1206 μg/g, and also significantly reduced larval growth (>75% versus controls) at concentrations of > 600 μg/g. The unsaturated analogs 2-(1E-pentadecenyl)furan and 2-(8Z, 11Z-heptadecadienyl)furan were less toxic. Triolein was only weakly toxic, with an LC50 value of 10,364 μg/g diet. Larval growth was inhibited only at concentrations of 7000 μg/g or higher. The potential of avocadofurans in insect control is discussed.
Thallium(I) Carboxylate Modification of the Hunsdiecker Reaction
Cambie, Richard C.,Hayward, Rodney C.,Jurlina, Jeffrey L.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 2608 - 2614 (2007/10/02)
Treatment of a thallium(I) carboxylate with 1 molar equivalent of bromine gives the corresponding thallium(III) carboxylate dibromide.High yields of primary alkyl bromides are obtained if the thallium(III) carboxylate dibromide is treated with 0.5 mol equiv. of bromine in refluxing carbon tetrachloride.Pyrolysis of the thallium(III) derivative in the absence of added bromine gives a low yield of the corresponding alkyl bromide.The use of thallium(I) carboxylates for the preparation of alkyl bromides in high yields is limited to the salts of primary carboxylic acids.A simple procedure for the preparation of alkyl bromides from carboxylic acids using thallium(I) carbonate has been developed.
