132431-12-0Relevant articles and documents
Gold-Catalyzed Friedel–Crafts-Like Reaction of Benzylic Alcohols to Afford 1,1-Diarylalkanes
Oakley, James V.,Stanley, Tyler J.,Jesse, Kate A.,Melanese, Amanda K.,Alvarez, Araceli A.,Prince, Aloha L.,Cain, Stephanie E.,Wenzel, Anna G.,Iafe, Robert G.
, p. 7063 - 7066 (2019)
A gold-catalyzed, Friedel–Crafts-like benzylation of unactivated benzylic alcohols to form 1,1-diarylalkanes has been developed. The operationally convenient method uses only 1.3 equivalents of the electron-rich arene, employs readily available starting m
Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles
Maier, Alexander F. G.,Tussing, Sebastian,Schneider, Tobias,Fl?rke, Ulrich,Qu, Zheng -Wang,Grimme, Stefan,Paradies, Jan
supporting information, p. 12219 - 12223 (2016/10/13)
An acceptorless dehydrogenation of heterocycles catalyzed by frustrated Lewis pairs (FLPs) was developed. Oxidation with concomitant liberation of molecular hydrogen proceeded in high to excellent yields for N-protected indolines as well as four other substrate classes. The mechanism of this unprecedented FLP-catalyzed reaction was investigated by mechanistic studies, characterization of reaction intermediates by NMR spectroscopy and X-ray crystal analysis, and by quantum-mechanical calculations. Hydrogen liberation from the ammonium hydridoborate intermediate is the rate-determining step of the oxidation. The addition of a weaker Lewis acid as a hydride shuttle increased the reaction rate by a factor of 2.28 through a second catalytic cycle.
Approach to the synthesis of indoline derivatives from diaryliodonium salts
Landge, Kamalkishor P.,Jang, Keun Sam,Lee, Sang Yeul,Chi, Dae Yoon
, p. 5705 - 5713 (2012/09/07)
An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indoline compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.
Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature
Yan, Chang-Song,Peng, Yu,Xu, Xiao-Bo,Wang, Ya-Wen
, p. 6039 - 6048 (2012/06/18)
A nickel-mediated intermolecular reductive cross-coupling reaction of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclization-intermolecular cross-coupling. Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to these useful building blocks, which would be potentially valuable in the synthesis of relevant natural products. A rational explanation for the formation of contiguous stereogenic centers is given. Copyright
INHIBITION OF BACTERIAL BIOFILMS WITH ARYL CARBAMATES
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Page/Page column 33, (2012/02/01)
Disclosure is provided for carbamate compounds that prevent, remove and/or inhibit the formation of biofilms, compositions including these compounds, devices including these compounds, and methods of using the same.
A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc
Kubo, Tetsuji,Katoh, Chiharu,Yamada, Ken,Okano, Kentaro,Tokuyama, Hidetoshi,Fukuyama, Tohru
supporting information; experimental part, p. 11230 - 11236 (2009/04/11)
A unique combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 °C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical N,N′-dialkylated phenylenediamines, was investigated.
Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction
Minatti, Ana,Buchwald, Stephen L.
supporting information; experimental part, p. 2721 - 2724 (2009/05/27)
(Chemical Equation Presented) A highly efficient one-pot procedure for the synthesis of indolines and their homologues based on a domino Cu-catalyzed amidation/nucleophilic substitution reaction has been developed. Substituted 2-iodophenethyl mesylates and related compounds afforded the corresponding products in excellent yields. No erosion of optical purity was observed when transforming enantiomerically pure mesylates under the reaction conditions.
Synthesis of novel phenylnaphthyl phosphines and their applications to Pd-catalyzed intramolecular amidation
Kitamura, Yuki,Hashimoto, Ayano,Yoshikawa, Seiji,Odaira, Jun-Ichi,Furuta, Takumi,Kan, Toshiyuki,Tanaka, Kiyoshi
, p. 115 - 117 (2007/10/03)
Novel phenylnaphthyl phosphines were prepared and applied to the Pd-catalyzed intramolecular amidation. Both ligands gave good to excellent yields in the synthesis of five-, six-, and seven-membered rings from halo-amides and carbamates. Georg Thieme Verl
Mild and selective deprotection of carbamates with Bu4NF
Jacquemard, Ulrich,Bénéteau, Valérie,Lefoix, Myriam,Routier, Sylvain,Mérour, Jean-Yves,Coudert, Gérard
, p. 10039 - 10047 (2007/10/03)
A new mild method allowing the removal of carbamates using TBAF in THF is reported. Reactions were performed on indole, indoline, N-methyl aniline, aniline and tryptamine derivatives. The observed selectivity according to the carbamates or the substrates is discussed. A mechanism is postulated. Graphical Abstract
A mild copper-mediated intramolecular amination of aryl halides
Yamada, Ken,Kubo, Tetsuji,Tokuyama, Hidetoshi,Fukuyama, Tohru
, p. 231 - 234 (2007/10/03)
A unique combination of copper iodide and cesium acetate was found to mediate intramolecular amination of aryl halides under mild conditions. The reaction proceeds at room temperature with primary or N-benzyl amines and at moderately elevated temperatures with other amine derivatives. The reaction has been applied to the formation of 5-, 6-, and 7-membered rings. Remarkably, halogens at the meta-position were retained, providing a definitive advantage over palladium-catalyzed systems.
