1595-07-9Relevant academic research and scientific papers
Rhodium-Catalyzed Alkenylation of Toluene Using 1-Pentene: Regioselectivity to Generate Precursors for Bicyclic Compounds
Liebov, Nichole S.,Zhu, Weihao,Chen, Junqi,Webster-Gardiner, Michael S.,Schinski, William L.,Gunnoe, T. Brent
supporting information, p. 3844 - 3851 (2019/10/16)
Rhodium catalysts for arene alkenylation reported by our group (e.g., Science 2015, 348, 421; J. Am. Chem. Soc. 2017, 139, 5474; J. Am. Chem. Soc. 2018, 140, 17007) have demonstrated selectivity for 1-aryl alkenes over y-aryl alkenes (y > 1). This selectivity is notable because 1-aryl alkenes or 1-aryl alkanes cannot be generated using acid-based Friedel-Crafts arene alkylation or acidic zeolite catalysts. Herein, we report the extension of Rh arene alkenylation catalysis to generate 1-tolyl-1-pentenes, which are potential precursors for bicyclic compounds. The olefin concentration, copper(II) oxidant identity and concentration, reaction temperature, and rhodium concentration for the alkenylation of toluene with 1-pentene have been optimized using [Rh(Η2-C2H4)2(μ-OAc)]2 as the catalyst precursor. The rhodium-based catalysis achieves up to 12(1):1 anti-Markovnikov selectivity for 1-tolyl-1-pentenes over 2-tolyl-2-pentenes and is selective for alkenylation in the meta and para positions.
Terminal-Selective Functionalization of Alkyl Chains by Regioconvergent Cross-Coupling
Dupuy, Stéphanie,Zhang, Ke-Feng,Goutierre, Anne-Sophie,Baudoin, Olivier
supporting information, p. 14793 - 14797 (2016/11/23)
Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C?H bond functionalization methods. We describe herein a new step-economical approach that enables C?C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alkyl zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross-coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross-coupling then provided access to the corresponding linear arylation product in only two steps.
Transfer hydrogenation of alkenes using Ni/Ru/Pt/Au heteroquatermetallic nanoparticle catalysts: Sequential cooperation of multiple nano-metal species
Ito, Yoshikazu,Ohta, Hidetoshi,Yamada, Yoichi M. A.,Enoki, Toshiaki,Uozumi, Yasuhiro
supporting information, p. 12123 - 12126 (2015/02/19)
Quatermetallic alloy nanoparticles of Ni/Ru/Pt/Au were prepared and found to promote the catalytic transfer hydrogenation of non-activated alkenes bearing conjugating units (e.g., 4-phenyl-1-butene) with 2-propanol, where the composition metals, Ni, Ru, Pt, and Au, act cooperatively to provide significant catalytic ability. This journal is
Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes
Ahuja, Ritu,Punji, Benudhar,Findlater, Michael,Supplee, Carolyn,Schinski, William,Brookhart, Maurice,Goldman, Alan S.
experimental part, p. 167 - 171 (2012/03/27)
Aromatic hydrocarbons are among the most important building blocks in the chemical industry. Benzene, toluene and xylenes are obtained from the high temperature thermolysis of alkanes. Higher alkylaromatics are generally derived from arene-olefin coupling, which gives branched products-that is, secondary alkyl arenes-with olefins higher than ethylene. The dehydrogenation of acyclic alkanes to give alkylaromatics can be achieved using heterogeneous catalysts at high temperatures, but with low yields and low selectivity. We present here the first catalytic conversion of n-alkanes to alkylaromatics using homogeneous or molecular catalysts-specifically 'pincerg'-ligated iridium complexes-and olefinic hydrogen acceptors. For example, the reaction of n-octane affords up to 86% yield of aromatic product, primarily o-xylene and secondarily ethylbenzene. In the case of n-decane and n-dodecane, the resulting alkylarenes are exclusively unbranched (that is, n-alkyl-substituted), with selectivity for the corresponding o-(n-alkyl)toluene.
Use of tetrahydropyridine derivatives to prepare medicines for treating diseases causing demyelination
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, (2008/06/13)
The invention relates to the use of tetrahydropyridine derivatives of the formula in which: R1is a halogen or a CF3, (C1-C4)alkyl or (C1-C4)alkoxy group; Y is a nitrogen atom or a CH group;
Use of 4-substituted tetrahydropyridines for making medicines acting on TGF-β1
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Page column 15-16, (2010/02/04)
The invention relates to the use of a compound of formula (I): for the preparation of pharmaceutical compositions for increasing the circulating, cellular and extracellular levels of TGF-β1.
1-Phenylalkyl-1,2,3,6-tetrahydropyridines for treating Alzheimer's disease
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, (2008/06/13)
PCT No. PCT/FR97/02286 Sec. 371 Date Jul. 27, 1999 Sec. 102(e) Date Jul. 27, 1999 PCT Filed Dec. 12, 1997 PCT Pub. No. WO98/25903 PCT Pub. Date Jun. 18, 1998The invention relates to compounds of the formula in which: Y is -CH- or -N-; R1 is hydrogen, a ha
METAL COMPLEXES IN ORGANIC SYNTHESIS. VIII. ALLYLIC ALCOHOLS AS STARTING MATERIALS IN PALLADIUM-CATALYZED WITTIG-TYPE OLEFINIZATIONS.
Moreno-Manas,Truis
, p. 2154 - 2158 (2007/10/02)
Allylic alcohols, aldehydes, and triphenylphosphine participate in a one-pot process catalyzed by palladium, which is formally equivalent to the Wittig olefinization. It can be applied to both aliphatic and aromatic aldehydes. The resulting olefins which appear as mixtures of stereoisomers were fully hydrogenated. Two different mechanisms can account for the observed results.
