- Stereoselective Aminoiodination of Activated Alkynes with Organoiodine(III) Reagents and Amines via Multiple-Site Functionalization: Access to Iodinated Enamines and N-Aryl Indoles
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A stereoselective aminoiodination of activated alkynes with PhI(OAc)2 and amines via multiple-site functionalization to afford (Z)diethyl 2-(diphenylamino)-3-iodomaleate derivatives with superior yields has been described. The key feature of th
- Arepally, Sagar,Chamuah, Ajoy,Katta, Narenderreddy,Sharada, Duddu S.
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p. 1542 - 1547
(2019/02/03)
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- Oxidative Decarboxylation Enables Chemoselective, Racemization-Free Esterification: Coupling of α-Ketoacids and Alcohols Mediated by Hypervalent Iodine(III)
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An α-ketoacid could be converted into a reactive acylating agent by treatment with hypervalent iodine(III) species, and in so doing, we discovered a novel decarboxylative acylation of alcohols that affords a variety of esters in excellent yields. The esterification has been applied to a sterol bearing a free carboxylic acid and shows unique chemoselectivity. The procedure is racemization-free and operates under mild conditions.
- Nanjo, Takeshi,Kato, Natsuki,Takemoto, Yoshiji
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p. 5766 - 5769
(2018/09/12)
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- Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
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A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).
- Zhao, Chun-Yang,Li, Kun,Pang, Yu,Li, Jia-Qing,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
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supporting information
p. 1919 - 1925
(2018/03/28)
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- Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate
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A practical method for the preparation of (diacetoxyiodo)arene ArI(OAc)2 is described. The use of commercially available sodium hypochlorite pentahydrate (NaClO·5H2O) enabled safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing and -donating substituents. The method allows tandem divergent access to synthetically useful organo-λ3-iodanes such as hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.
- Watanabe, Ayumi,Miyamoto, Kazunori,Okada, Tomohide,Asawa, Tomotake,Uchiyama, Masanobu
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p. 14262 - 14268
(2018/11/23)
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- An Investigation of (Diacetoxyiodo)arenes as Precursors for Preparing No-Carrier-Added [18F]Fluoroarenes from Cyclotron-Produced [18F]Fluoride Ion
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Treatment of (diacetoxyiodo)arenes (1a-1u) with cyclotron-produced [18F]fluoride ion rapidly affords no-carrier-added [18F]fluoroarenes (2a-2u) in useful yields and constitutes a new method for converting substituted iodoarenes into substituted [18F]fluoroarenes in just two steps.
- Haskali, Mohammad B.,Telu, Sanjay,Lee, Yong-Sok,Morse, Cheryl L.,Lu, Shuiyu,Pike, Victor W.
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p. 297 - 302
(2016/01/15)
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- Tandem catalytic C(sp3)-H amination/sila-sonogashira-hagihara coupling reactions with iodine reagents
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A new tandem C-N and C-C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations. I(003) is a double agent: A tandem C-N and C-C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process affords complex building blocks with high yields, and demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations.
- Buendia, Julien,Darses, Benjamin,Dauban, Philippe
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supporting information
p. 5697 - 5701
(2015/06/16)
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- Simple and practical method for preparation of [(diacetoxy)iodo]arenes with iodoarenes and m-chloroperoxybenzoic acid
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Various [(diacetoxy)iodo]arenes bearing 4-methylphenyl, phenyl, 4-nitrophenyl, 3-nitrophenyl, 4-cyanophenyl, 4-bromophenyl, 4- methoxycarbonyphenyl, 3,5-bis(trifluoromethyl)phenyl, and 4-(N,N,N- trimethylammonium)methylphenyl groups were efficiently prepared by the treatment of iodoarenes with m-chloroperoxybenzoic acid in acetic acid. The great advantage of the present method is the easy preparation and isolation of [(diacetoxy)-iodo]arenes bearing electron-withdrawing groups, such as 4-nitro, 4-cyano, 4-methoxycarbonyl, and 3,5-bis(trifluoromethyl) groups, on the aromatic ring.
- Iinuma, Masataka,Moriyama, Katsuhiko,Togo, Hideo
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p. 2663 - 2666,4
(2012/12/12)
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- Rapid and efficient radiosyntheses of meta-substituted [ 18F]fluoroarenes from [18F]fluoride ion and diaryliodonium tosylates within a microreactor
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Effective methods for the introduction of the short-lived positron-emitter fluorine-18 (t1/2 = 109.7 min) at high specific radioactivity into fluoroarenes are valuable for the development of radiotracers for molecular imaging with positron emis
- Chun, Joong-Hyun,Lu, Shuiyu,Pike, Victor W.
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experimental part
p. 4439 - 4447
(2011/10/08)
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- 4-ARYLOXYQUINOLIN-2(1H)-ONES AS MTOR KINASE AND PI3 KINASE INHIBITORS, FOR USE AS ANTI-CANCER AGENTS
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4-aryloxyquinolin-2(1H)-ones as mtor kinase and PI3 kinase inhibitors, for use as anti-cancer agents. Compounds of the formula I and pharmaceutically acceptable salts thereof, wherein A, B, R1, R2, R3, R4, R5, R6, and R7 are defined as set forth herein are disclosed. Also disclosed are pharmaceutical compositions comprising the compounds of the invention and a pharmaceutically acceptable carrier, methods of making the compounds of the invention and methods of using the compounds for inhibiting mTOR and PI3 kinases and for treating cancers.
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Page/Page column 60
(2010/04/06)
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- Unexpected, drastic effect of triflic acid on oxidative diacetoxylation of iodoarenes by sodium perborate. A facile and efficient one-pot synthesis of (diacetoxyiodo) arenes
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An easy, safe, and effective method for preparing (diacetoxyiodo)arenes from iodoarenes is presented. Addition of trifluoromethanesulfonic acid (triflic acid) as a promoter causes a drastic increase in the yield of (diacetoxyiodo)arenes in the reaction of iodoarenes with sodium perborate. The reaction of the iodoarenes with sodium perborate in acetic acid in the presence of triflic acid at 40-45 °C efficiently generates the corresponding (diacetoxyiodo)arenes in high yields within short time.
- Hossain, Md. Delwar,Kitamura, Tsugio
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p. 6984 - 6986
(2007/10/03)
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- Alternative, easy preparation of (diacetoxyiodo)arenes from iodoarenes using potassium peroxodisulfate as the oxidant
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An easy, safe and effective method for preparing (diacetoxyiodo)arenes [ArI(OAc)2], from iodoarenes is presented in this paper, using potassium peroxodisulfate as the oxidant. This procedure avoids the use of high temperature and severe reaction conditions. The reaction of the iodoarenes with potassium peroxodisulfate in acetic acid in the presence of concentrated sulfuric acid or trifluoromethane sulfonic acid at room temperature, efficiently generates the corresponding (diacetoxyiodo)arenes in high yield in a short reaction time. Georg Thieme Verlag Stuttgart.
- Hossain, Md. Delwar,Kitamura, Tsugio
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p. 1932 - 1934
(2007/10/03)
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- FURTHER FUNCTIONAL GROUP OXIDATIONS USING SODIUM PERBORATE
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Sodium perborate in acetic acid is an effective reagent for the oxidation of aromatic aldehydes to carboxylic acids, iodoarenes to (diacetoxyiodo)arenes, azines to N-oxides, and various types of sulfur heterocycles to S,S-dioxides.Nitriles are unaffected by the reagent in acetic acid, but undergo smooth hydration to amides when aqueous methanol is employed as solvent.
- McKillop, Alexander,Kemp, Duncan
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p. 3299 - 3306
(2007/10/02)
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