- Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis
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A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.
- García Manche?o, Olga,Kuhlmann, Jan H.,Pérez-Aguilar, María Carmen,Piekarski, Dariusz G.,Uygur, Mustafa
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supporting information
p. 3392 - 3399
(2021/05/21)
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- Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
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The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.
- Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang
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supporting information
p. 18118 - 18127
(2020/11/26)
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- BRM TARGETING COMPOUNDS AND ASSOCIATED METHODS OF USE
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The present disclosure relates to bifunctional compounds, which find utility as modulators of SMARCA2 or BRM (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a ligand that binds to the Von Hippel-Lindau E3 ubiquitin ligase, and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.
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Paragraph 1073-1074
(2019/10/23)
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- Multienzyme One-Pot Cascade for the Stereoselective Hydroxyethyl Functionalization of Substituted Phenols
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The operability and substrate scope of a redesigned vinylphenol hydratase as a single biocatalyst or as part of multienzyme cascades using either substituted coumaric acids or phenols as stable, cheap, and readily available substrates are reported.
- Payer, Stefan E.,Pollak, Hannah,Schmidbauer, Benjamin,Hamm, Florian,Juri?i?, Filip,Faber, Kurt,Glueck, Silvia M.
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supporting information
p. 5139 - 5143
(2018/09/13)
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- Synthetic method for rugchalcone A, B and their derivatives and their anti-inflammatory use
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The present invention provides an effective anti-inflammatory agent which does not have a side effect. The present inventors have invented an effective method for synthesizing 2-aroylbenzofuran, rugchalcone A, B, and a derivative thereof at high yield by a Rap-Stoermer reaction between substituted salicylaldehyde and phenacyl bromide. Moreover, the inventors have evaluated an anti-inflammatory effect of the compound in lipopolysaccharide-induced RAW 264.7 macrophages. The compound remarkably inhibits the generation of nitrogen oxide which mediates inflammation without having cytotoxicity at a concentration of 10 andmu;M, and an IC_50 value is in the range of 0.57-13.27 andmu;M. From 2-aroylbenzofuran synthesized according to the preset invention, compound 4 (99.6%; IC_50 = 0.57), rugchalcone B (compound 2)(99.3%; IC_50 = 4.13), compound 7 (96.8%; IC_50 = 1.90), and compound 8 (74.3%; IC_50 = 0.99) show a maximum inhibiting activity. Such a result shows that compounds 2, 4, 7, and 8 having 4-hydroxyphenyl group and/or a hydroxyl group in a 5- and/or 6- position of a benzofuran motif can be functioned as a structure needed in developing an iNOS inhibitor with respect to the application thereof to the anti-inflammatory field.COPYRIGHT KIPO 2017
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Paragraph 0059-0060
(2017/08/09)
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- Platinum(ii) O,S complexes as potential metallodrugs against Cisplatin resistance
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We report on platinum(ii) complexes with different cinnamic acid derivatives as ligands with cytotoxic activity against Cisplatin resistant ovarian cancer cell line subcultures of SKOV3 and A2780. A typical mechanism of action for platinum(ii) complexes a
- Hildebrandt, Jana,H?fner, Norman,G?rls, Helmar,Kritsch, Daniel,Ferraro, Giarita,Dürst, Matthias,Runnebaum, Ingo B.,Merlino, Antonello,Weigand, Wolfgang
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supporting information
p. 18876 - 18891
(2016/12/09)
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- Synthesis and biological evaluation of 2-aroylbenzofurans, rugchalcones A, B and their derivatives as potent anti-inflammatory agents
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An efficient synthesis of 2-aroylbenzofurans, rugchalcones A, B and their derivatives was accomplished in excellent yields by the Rap–Stoermer reaction between substituted salicylaldehydes and phenacyl bromides. Later their anti-inflammatory effects were evaluated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. The compounds were exhibited exceptional potency against inflammatory mediated NO production with no cytotoxicity at 10?μM concentration and IC50values are found in the range from 0.75 to 13.27?μM. Among the 2-aroylbenzofurans prepared in this study, compounds 4 (99.6%; IC50?=?0.57), rugchalcone B (2) (99.3%; IC50?=?4.13), 7 (96.8%; IC50?=?1.90) and 8 (74.3%; IC50?=?0.99) were showed the maximum inhibitory activity. This study suggests that compounds 2, 4, 7 and 8 which are having 4-hydroxyphenyl group and/or hydroxy (–OH) group at 5- and/or 6-position of benzofuran motif could be considered as a promising scaffolds for the further development of iNOS inhibitors for potential anti-inflammatory applications.
- Seo, Young Hwa,Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
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supporting information
p. 1521 - 1524
(2016/07/29)
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- Platinum(II) Complexes with O,S Bidentate Ligands: Biophysical Characterization, Antiproliferative Activity, and Crystallographic Evidence of Protein Binding
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We recently characterized a series of novel platinum(II) compounds bearing a conserved O,S binding moiety as a bifunctional ligand and evaluated their solution behavior and antiproliferative properties in vitro against a representative cancer cell line. O
- Mügge, Carolin,Marzo, Tiziano,Massai, Lara,Hildebrandt, Jana,Ferraro, Giarita,Rivera-Fuentes, Pablo,Metzler-Nolte, Nils,Merlino, Antonello,Messori, Luigi,Weigand, Wolfgang
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p. 8560 - 8570
(2015/09/21)
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- Pyrazole-5-carboxamides, novel inhibitors of receptor for advanced glycation end products (RAGE)
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In an effort to develop novel inhibitors of receptor for advanced glycation end products (RAGE) for the treatment of Alzheimer's disease, a series of pyrazole-5-carboxamides were designed, synthesized and biologically evaluated. Analyses of the extensive
- Han, Young Taek,Kim, Kyeojin,Choi, Gyeong-In,An, Hongchan,Son, Dohyun,Kim, Hee,Ha, Hee-Jin,Son, Jun-Hyeng,Chung, Suk-Jae,Park, Hyun-Ju,Lee, Jeewoo,Suh, Young-Ger
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p. 128 - 142
(2014/05/06)
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- Environmentally benign deprotection of dithioacetals using 30% hydrogen peroxide catalyzed by Fe(acac)3 and sodium iodide
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The reaction of dithioacetals with 30% hydrogen peroxide in the presence of catalytic amounts of iron(III) acetylacetonate and sodium iodide efficiently produced the corresponding carbonyl compounds in high yields.
- Kirihara, Masayuki,Suzuki, Satoshi,Ishizuka, Yuki,Yamazaki, Kento,Matsushima, Ryoji,Suzuki, Takaya,Iwai, Toshiaki
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p. 5477 - 5480
(2013/09/23)
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- Deprotection of dithioacetals with 30% hydrogen peroxide catalyzed by tantalum(V) chloride-sodium iodide or niobium(V) chloride-sodium iodide
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The reaction of dithioacetals with 30% hydrogen peroxide in the presence of catalytic amounts of tantalum(V) and iodide ion effectively produced carbonyl compounds in high yields. Dithioacetals also can be deprotected using the niobium(V) catalyzed oxidation of iodide ion by hydrogen peroxide under mild conditions.
- Kirihara, Masayuki,Noguchi, Takuya,Okajima, Nobuhiro,Naito, Sayuri,Ishizuka, Yuki,Harano, Aiko,Tsukiji, Hiroyuki,Takizawa, Ryu
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experimental part
p. 1515 - 1520
(2012/03/07)
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- ARYLPYRAZOLES AND ARYLISOXAZOLES AND THEIR USE AS PKD MODULATORS
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The present invention provides novel organic compounds of formula (I) or (Ia): which may be inhibitors of a selective subset of kinases belonging to the AGC or calmodulin kinase family, such as for example PKD-1/2/3, inhibitors of histone deacetylase (HDA
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Page/Page column 96
(2011/02/24)
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- An atom-efficient and powerful method for direct esterification of silyl ethers catalyzed by HClO4-SiO2
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An efficient and convenient procedure for direct esterification of alkyl and aryl silyl ethers with Ac2O and a catalyst system of perchloric acid immobilized on a silica gel (HClO4-SiO2) has been developed. The silyl protecting groups are directly replaced by acetyls and the protecting groups themselves are transformed into acetates as the sole byproducts, which can be readily recovered and converted back to silylchlorides, the original protecting agents, thus minimizing wastes.
- Du, Ti-Jian,Wu, Qin-Pei,Liu, Hai-Xia,Chen, Xi,Shu, Yi-Nan,Xi, Xiao-Dong,Zhang, Qing-Shan,Li, Yun-Zheng
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experimental part
p. 1096 - 1101
(2011/04/16)
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- TEMPO-linked metalloporphyrins as efficient catalysts for selective oxidation of alcohols and sulfides
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Six new TEMPO-linked porphyrins and metalloporphyrins were synthesized and they exhibited efficient catalytic activity for selective oxidation of alcohols and sulfides to the corresponding aldehydes, ketones and sulfoxides using NaOCl as oxidant.
- Huang, Jian-Ying,Li, Shi-Jun,Wang, Yan-Guang
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p. 5637 - 5640
(2007/10/03)
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- Direct synthesis of carbonyl compounds from THP ethers with IBX in the presence of β-cyclodextrin in water
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Water, an environmentally friendly reaction medium, has been utilized for the oxidative deprotection of tetrahydropyranyl ethers 1 with IBX at room temperature in the presence of β-cyclodextrin to give the corresponding carbonyl compounds 2.
- Narender,Reddy, M. Somi,Kumar, V. Pavan,Nageswar,Rao, K. Rama
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p. 1971 - 1973
(2007/10/03)
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- Cytokine inhibitors
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Disclosed are compounds of formula (I) which inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclos
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Page/Page column 29-30
(2008/06/13)
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- Deprotection of dithioacetals using the tantalum(V) chloride catalyzed oxidation of iodide ion by hydrogen peroxide
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Dithioacetals can be deprotected to afford carbonyl groups using the tantalum(V) chloride catalyzed oxidation of iodide ion by hydrogen peroxide under mild conditions.
- Kirihara, Masayuki,Harano, Aiko,Tsukiji, Hiroyuki,Takizawa, Ryu,Uchiyama, Tomoyuki,Hatano, Akihiko
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p. 6377 - 6380
(2007/10/03)
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- A mild and efficient oxidative deprotection of THP ethers with NBS in the presence of β-cyclodextrin in water
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An efficient and user-friendly procedure has been developed for the oxidative deprotection of tetrahydropyranyl (THP) ethers with N-bromosuccinimide (NBS) using β-cyclodextrin (β-CD) in water. A series of tetrahydropyranyl ethers were oxidatively deprotected at room temperature in impressive yields.
- Narender,Somi Reddy,Rama Rao
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p. 1741 - 1743
(2007/10/03)
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- Cytokine inhibitors
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Disclosed are compounds of formula (I) Where Ar1, X, Y, Q, W, R3, R4, R5, R6 and Ry are defined herein. The compounds of the invention inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. The compounds are also useful for treating diseases or conditions related to oncology and anticoagulant or fibrinolytic therapy. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.
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Page/Page column 66
(2010/02/08)
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- Cytokine inhibitors
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Disclosed are compounds of formula (I) Where Ar1, X, R3, R4, R5 and R6 are defined herein. The compounds of the invention inhibit production of cytokines involved in inflammatory processes and are thu
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- Secondary Benzylation Using Benzyl Alcohols Catalyzed by Lanthanoid, Scandium, and Hafnium Triflate
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The combination of a secondary benzyl alcohol and a metal triflate (e.g., La, Yb, Sc, and Hf triflate) in nitromethane was a highly effective secondary-benzylation system. Secondary benzylation of carbon (aromatic compounds, olefins, an enol acetate), nitrogen (amide derivatives), and oxygen (alcohols) nucleophiles was carried out with a secondary benzyl alcohol and 0.01-1 mol % of a metal triflate in the presence of water. Secondary benzyl alcohols and nucleophiles bearing acid-sensitive functional groups (e.g., tert-butyldimethylsilyloxy and acetoxy groups and methyl and benzyl esters) could be used for alkylation. Hf(OTf)4 was the most active catalyst for this alkylation, and trifluoromethanesulfonic acid (triflic acid, TfOH) was also a good catalyst. The catalytic activity of metal triflates and TfOH increased in the order La(OTf)3 3 3 4. A mechanistic study was also performed. The reaction of 1-phenylethanol (4a) in the presence of Sc(OTf) 3 in nitromethane gave an equilibrium mixture of 4a and bis(1-phenylethyl) ether (54). Addition of a carbon nucleophile to the equilibrium mixture gave alkylated product in high yield.
- Noji, Masahiro,Ohno, Tomoko,Fuji, Koji,Futaba, Noriko,Tajima, Hiroyuki,Ishii, Keitaro
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p. 9340 - 9347
(2007/10/03)
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- Synthesis, stereochemistry confirmation and biological activity evaluation of a constituent from Isodon excisus
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A synthesis and stereochemistry confirmation of a constituent recently isolated from the whole plant Isodon excisus is reported. An enantioselective catalytic boron-mediated reduction of an α-bromoketone was utilized in the key synthetic transformation. The methodology described herein was also used for the synthesis of the natural product's enantiomer and several derivatives. In addition, the compounds were evaluated for inhibitory activity in a caspase induction assay. The natural product was found to be devoid of activity, but several derivatives had moderate inhibitory activity (EC 501 μM).
- Xing, Xuechao,Ho, Pei,Bourquin, Geoffroy,Yeh, Li-An,Cuny, Gregory D.
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p. 9961 - 9969
(2007/10/03)
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- Total synthesis of (±)-Aiphanol, a novel cyclooxygenase-inhibitory stilbenolignan
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(±)-Aiphanol has been stereoselectively synthesized through IBX-mediated o-quinone formation, and through [4+2] cycloaddition of the o-quinone and cinnamyl alcohol unit.
- Kuboki, Atsuhito,Yamamoto, Toru,Ohira, Susumu
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p. 420 - 421
(2007/10/03)
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- A novel, efficient, and selective cleavage of acetals using bismuth(III) chloride
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Treatment of acetals with bismuth(III) chloride in methanol provides a simple, convenient and chemoselective process for deprotection, and the parent aldehyde or ketone was obtained in high yield. The acetals have been cleaved selectively in the presence of silyl, benzyl and tetrahydropyranyl ethers.
- Sabitha, Gowravaram,Babu, R. Satheesh,Reddy, E. Veakata,Yadav
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p. 1074 - 1075
(2007/10/03)
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- DDQ as a versatile reagent for oxidative cleavage of tosylhydrazones and oximes
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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was found to be a very efficient oxidative reagent for the selective cleavage of tosylhydrazones and oximes of carbonyl compounds for the first time.
- Chandrasekhar,Reddy, Ch. Raji,Reddy, M. Venkat
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p. 430 - 431
(2007/10/03)
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- Facile methods for the direct conversions of aryl acetates into the corresponding methoxymethyl ethers or silyl ethers
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Direct conversion of aryl acetates into aryl methoxymethyl ethers or aryl trialkylsilyl ethers was readily accomplished by treatment with methoxymethyl bromide or trialkylsilyl trifluoromethanesulfonate, respectively, in the presence of sodium methoxide.
- Oriyama, Takeshi,Noda, Kojiro,Sugawara, Satomi
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p. 2217 - 2223
(2007/10/03)
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- Nonionic superbase-catalyzed silylation of alcohols
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Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)3N, 1b, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 °C and on rare occasions in DMF from 24 to 80 °C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of lb as a catalyst, tertiary alcohols were recovered unchanged.
- D'Sa, Bosco A.,McLeod, Dale,Verkade, John G.
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p. 5057 - 5061
(2007/10/03)
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- Preparation of allyl-, alkenyl- and of functionalized arylmanganese reagents by oxidative insertion of manganese-graphite into organic halides
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Reduction of MnBr2·nLiBr (n = 1,2) with 2 C8K in THF affords highly active Mn-graphite, which readily insert into allyl-, alkenyl-, (substituted) aryl- and heteroaryl halides. The functionalized organomanganese compounds thus obtained may be efficiently trapped with different electrophiles such as aldehydes, anhydrides and acid chlorides, or can be cross-coupled with alkenyl halides in the presence of catalytic amounts of Fe(acac)3.
- Fuerstner, Alois,Brunner, Heiko
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p. 7009 - 7012
(2007/10/03)
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