- Synthesis of Axially Chiral Anilides Enabled by a Palladium/Ming-Phos-Catalyzed Desymmetric Sonogashira Reaction
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Atropisomeric anilides are one of important C—N axially chiral compounds. Compared with the N-terminal functionalization to prepare such compounds, C-terminal functionalization strategies have been rarely reported. We describe herein an efficient synthesis of axially chiral anilides enabled by Pd-catalyzed desymmetric Sonogashira cross-coupling reactions with the use of a newly identified Ming-Phos. Moderate to high yields with high enantioselectivities (up to 98% ee) were obtained.
- Yang, Bin,Yang, Junfeng,Zhang, Junliang
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supporting information
p. 317 - 322
(2021/12/23)
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- Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate
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Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N -acetyl- p -toluidine, electrophilic iodination is accompanied by a small extent of chlorination.
- Hussain, Anwar,Sarkar, Akash Mamon,Sereda, Grigoriy,Zefirov, Nikolai
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p. 1140 - 1146
(2020/04/01)
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- COMPOUND AND ORGANIC LIGHT EMITTING ELEMENT COMPRISING SAME
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Provided are a compound of Chemical Formula 1: wherein X1 to X4 are identical to or different from one another and are each independently O, S, NR2 or CR3R4, and a to d are each 0 or 1, with the proviso that 1≤a+b+c+d; R1 and R11 to R14 are identical to o
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Paragraph 0129-0131
(2020/07/23)
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- NEW COMPOUND
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PROBLEM TO BE SOLVED: To provide a new compound that does not have structural similarity to ceramide and has excellent CERT inhibitory activity. SOLUTION: The present invention provides a new compound of structural formula (I). A bond group -X- is cis-cyclopropyl-, R1, R2, R3, R4, and R5 independently represent a hydrogen atom, a halogen atom, a linear or branched C1-C8 alkyl group that may have a halogen atom, or OR6. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0316; 0330
(2019/11/26)
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- One-Pot Synthesis of Pyrrolo[3,2,1-kl]phenothiazines through Copper-Catalyzed Tandem Coupling/Double Cyclization Reaction
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A novel and efficient synthesis of pyrrolo[3,2,1-kl]phenothiazines has been developed through a Cu(I)-catalyzed tandem C-S coupling/double cyclization process. Using 2-alkynyl-6-iodoanilines and o-bromobenzenethiols as the starting materials, a wide range
- Tang, Jiaming,Xu, Bingqing,Mao, Xi,Yang, Hongyan,Wang, Xiaoxia,Lv, Xin
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p. 11108 - 11114
(2015/11/18)
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- A highly regioselective synthesis of N-acyl-2-acyl(aroyl)indolium Chloride through Palladium-Copper Catalysis Followed by Friedel-Crafts Reaction
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2-Trimethylsilylethynyl acetanilides, obtained from the palladium-catalyzed reactions of 2-iodoacetanilides with trimethylsilylacetylene, underwent Friedel-Crafts acylation reactions yielding the N-acyl-2-acyl(aroyl)indolium chlorides in good yields. Georg Thieme Verlag Stuttgart New York.
- Khan, Md. Wahab,Akther, Arifa,Alam, Md. Shariful
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supporting information
p. 831 - 834
(2014/04/17)
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- Synthesis and structural insights of substituted 2-iodoacetanilides and 2-iodoanilines
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This study reports a simple and efficient method for the direct iodination of substituted anilines with molecular iodine and copper acetate in acetic acid producing 2-iodoacetanilies and 2-iodoanilines. Employing density functional theory (B3LYP) and MidiX basis set, computational study is performed to calculate equilibrium geometries, IR vibrational frequencies, and thermodynamic properties including change of energy, enthalpy and Gibbs free energies. The optimized geometries indicated longer C-I bond distance (2.133 ?) which makes iodine slightly positive. The partial atomic charge profile and electrostatic potential further confirmed that most of the iodinated products are capable of forming a distinct halogen bonding . The thermodynamic properties disclosed that all iodination reactions are endothermic. Understanding the substituents' effect, molecular frontier orbital (MO) calculations are conducted finding the HOMO, LUMO and HOMO-LUMO gaps for all compounds. The MO calculations revealed that two electron-withdrawing iodine groups have significant influence on lowering the HOMO-LUMO gap compared to one iodine group in the products.
- Hoque, Mohammad Mazharol,Halim, Mohammad A.,Rahman, Mohammad Mizanur,Hossain, Mohammad Ismail,Khan, Md. Wahab
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p. 367 - 374
(2013/11/19)
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- A mild and convenient synthesis of 1,2,3-triiodoarenes via consecutive iodination/diazotization/iodination strategy
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A mild and convenient synthesis of 1,2,3-triiodoarenes has been developed. This method consists of two steps which can be performed on multigram scale with moderate to excellent yields. This report discloses a practical synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, operationally simple, scalable, and is easy to workup and to purify. We also report the first regioselective transmetalation reaction of 1,2,3-triiodoarenes to provide ortho-diiodoaryl derivatives, which are useful building blocks and indeed are hard to make by other means. CSIRO 2013.
- Al-Zoubi, Raed M.,Futouh, Hassan Abul,McDonald, Robert
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p. 1570 - 1575
(2014/01/23)
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- An all-photonic molecule-based parity generator/checker for error detection in data transmission
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The function of a parity generator/checker, which is an essential operation for detecting errors in data transmission, has been realized with multiphotochromic switches by taking advantage of a neuron-like fluorescence response and reversible light-induced transformations between the implicated isomers.
- Baelter, Magnus,Li, Shiming,Nilsson, Jesper R.,Andreasson, Joakim,Pischel, Uwe
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supporting information
p. 10230 - 10233
(2013/08/23)
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- Ecofriendly iodination of activated aromatics and coumarins using potassium iodide and ammonium peroxodisulfate
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An environmentally benign protocol for the iodination of activated aromatics, such as phenols, anilines, and hydroxycou-marins, using inexpensive commercially available potassium iodide and ammonium peroxodisulfate (1:2.5 molar equivalents per mole of substrate) in aqueous methanol (MeOH-H 2O, 6:1) at room temperature has been developed. The protocol provides for ortho-selective monoiodination as the predominant product without added acid and it is compatible with a number of common oxidizible functional groups, such as formyl, benzylic C-H, aromatic amines and hydroxymethyl. Good to acceptable yields of monoiodinated products in acceptable reaction times and exclusive ortho-iodination for 7-hydroxycoumarins, despite the presence of vinylogous electronrich C3, are some of the key advantageous features of the method. Georg Thieme Verlag Stuttgart.
- Ganguly, Nemai C.,Barik, Sujoy Kumar,Dutta, Sanjoy
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experimental part
p. 1467 - 1472
(2010/09/16)
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- Asymmetric radical and anionic cyclizations of axially chiral carbamates
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Standard Boc, Alloc, and Cbz derivatives of N-2,4-dimethyl-6-iodophenyl-N- allyl anilines are axially chiral and can be readily resolved into atropisomers whose racemization barriers exceed 30 kcal/mol. The resolved axially chiral carbamates undergo radic
- Guthrie, David B.,Curran, Dennis P.
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supporting information; experimental part
p. 249 - 251
(2009/06/28)
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- Convenient and efficient method for the iodination of aromatic amines by pyridinium iodochloride
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A simple and efficient method for the iodination of aromatic amines using pyridinium iodochloride (PyICl) in methanol as solvent is reported. Mild reaction conditions, short reaction time, and good to excellent yields of the product are the noteworthy advantages of the method. Pyridinium iodochloride is an efficient solid iodinating reagent and can be handled safely. Copyright Taylor & Francis Group, LLC.
- Khansole, Sandeep V.,Junne, Subhash B.,Sayyed, Mudassar A.,Vibhute, Yeshwant B.
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p. 1792 - 1798
(2008/09/20)
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- Highly chemoselective hydrogenolysis of iodoarenes
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The catalytic hydrodehalogenation reaction using molecular hydrogen and Pd/C has been revisited. It is shown that the speed of removal of halogen increases with increasing electronegativity I Br Cl. Nevertheless, selective dehydrohalogenation in compounds containing other reducible functions can be achieved only with iodine and not with bromine or chlorine. Selective deiodination of iodobenzophenone could be accomplished without reducing the carbonyl group. Hydrogenolysis of azidoiodoaromatic compounds to the corresponding azido compounds is high yielding. This selectivity was exploited for the labeling of benzophenone- and azido-containing compounds by deuterium and tritium.
- Faucher, Nicolas,Ambroise, Yves,Cintrat, Jean-Christophe,Doris, Eric,Pillon, Florence,Rousseau, Bernard
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p. 932 - 934
(2007/10/03)
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- Synthesis and magnetic behaviour of polyradical: Poly(1,3-phenyleneethynylene) with π-toporegulated pendant stable aminoxyl and imine N-oxide-aminoxyl radicals
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The palladium-catalysed polycondensation of N-tert-butyl-N-(3,5-diethynylphenyl)aminoxyl with 2-(3,5-diiodophenyl)-4,4,5,5-tetramethyl-3-oxido-2-imidazolin-3-ium-l-yloxyl in pyridine-triethylamine at room temperature afforded poly(l,3-phenyleneethynylene)
- Miura, Yozo,Issiki, Tsuneki,Ushitani, Yukio,Teki, Yoshio,Itoh, Koichi
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p. 1745 - 1750
(2007/10/03)
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- Halogenation Using Quaternary Ammonium Polyhalides. VII. Iodination of Aromatic Amines by Use of Benzyltrimethylammonium Dichloroiodate(1-)
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The reaction of aromatic amines with benzyltrimethylammonium dichloroiodate(1-) in dichloromethane-methanol in the presence of calcium carbonate powder for several hours at room temperature gave selectively iodo-substituted aromatic amines in good yields.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Yamasaki, Hiromichi,Fujisaki, Shizuo,Okamoto, Tsuyoshi
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p. 600 - 602
(2007/10/02)
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