- Gold-Catalyzed Friedel–Crafts-Like Reaction of Benzylic Alcohols to Afford 1,1-Diarylalkanes
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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
- 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.
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- Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles
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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.
- Maier, Alexander F. G.,Tussing, Sebastian,Schneider, Tobias,Fl?rke, Ulrich,Qu, Zheng -Wang,Grimme, Stefan,Paradies, Jan
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supporting information
p. 12219 - 12223
(2016/10/13)
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- INHIBITION OF BACTERIAL BIOFILMS WITH ARYL CARBAMATES
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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.
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Page/Page column 33
(2012/02/01)
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- Approach to the synthesis of indoline derivatives from diaryliodonium salts
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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.
- Landge, Kamalkishor P.,Jang, Keun Sam,Lee, Sang Yeul,Chi, Dae Yoon
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p. 5705 - 5713
(2012/09/07)
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- Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature
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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
- Yan, Chang-Song,Peng, Yu,Xu, Xiao-Bo,Wang, Ya-Wen
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p. 6039 - 6048
(2012/06/18)
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- A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc
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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.
- Kubo, Tetsuji,Katoh, Chiharu,Yamada, Ken,Okano, Kentaro,Tokuyama, Hidetoshi,Fukuyama, Tohru
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supporting information; experimental part
p. 11230 - 11236
(2009/04/11)
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- Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction
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(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.
- Minatti, Ana,Buchwald, Stephen L.
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supporting information; experimental part
p. 2721 - 2724
(2009/05/27)
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- Synthesis of novel phenylnaphthyl phosphines and their applications to Pd-catalyzed intramolecular amidation
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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
- Kitamura, Yuki,Hashimoto, Ayano,Yoshikawa, Seiji,Odaira, Jun-Ichi,Furuta, Takumi,Kan, Toshiyuki,Tanaka, Kiyoshi
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p. 115 - 117
(2007/10/03)
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- Mild and selective deprotection of carbamates with Bu4NF
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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
- Jacquemard, Ulrich,Bénéteau, Valérie,Lefoix, Myriam,Routier, Sylvain,Mérour, Jean-Yves,Coudert, Gérard
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p. 10039 - 10047
(2007/10/03)
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- A mild copper-mediated intramolecular amination of aryl halides
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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.
- Yamada, Ken,Kubo, Tetsuji,Tokuyama, Hidetoshi,Fukuyama, Tohru
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p. 231 - 234
(2007/10/03)
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- Pd/C(en)-catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations
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A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C-ethylenediamine [5% Pd/C(en)] and THF (or 1,4-dioxane) as a solvent, and the scope and limitations of this methodology were investigated. These results reinforce the utility of N-Cbz protective groups in synthetic chemistry, especially in peptide synthesis. (C) 2000 Elsevier Science Ltd.
- Hattori, Kazuyuki,Sajiki, Hironao,Hirota, Kosaku
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p. 8433 - 8441
(2007/10/03)
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- The development of efficient protocols for the palladium-catalyzed cyclization reactions of secondary amides and carbamates
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(equation presented) With the proper choice of palladium catalyst, ligand, and base, five-, six-, and seven-membered rings are formed efficiently from secondary amide or secondary carbamate precursors, offering significant improvements to currently existing methodology.
- Yang, Bryant H.,Buchwald, Stephen L.
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- Boron trifluoride promoted cleavage of benzyl carbamates
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A new efficient method for the cleavage of benzyl carbamates (CBZ protective groups) is described that involves a hard acid (BF3·OEt2) - soft nucleophile (EtSH) system. Unlike other available methods, this combination avoids the reduction of olefins, acetylenes, imines, halides and nitro groups, or the possibility of carboxylic ester hydrolysis.
- Subhas Bose,Thurston, David E.
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p. 6903 - 6906
(2007/10/02)
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