- Sequential Difunctionalization of 2-Iodobiphenyls by Exploiting the Reactivities of a Palladacycle and an Acyclic Arylpalladium Species
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A novel sequential difunctionalization reaction of 2-iodobiphenyl has been developed by exploiting the distinct reactivities of a palladacycle and an acyclic arylpalladium species. In this tandem reaction, an in situ formed dibenzopalladacyclopentadiene reacts selectively with an alkyl halide, after which the thus formed acyclic arylpalladium species selectively undergoes a Heck reaction with an alkene. This work demonstrates the strong relationship between the coordination mode of a transition metal complex and its reactivity, which could shed light on the mechanisms of other transition-metal-catalyzed reactions and offer the opportunity to develop other synthetically enabling organic transformations.
- Chen, Dushen,Shi, Guangfa,Jiang, Hang,Zhang, Yu,Zhang, Yanghui
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- Iodination of alkyl aryl ethers by mercury(II) oxide-iodine reagent in dichloromethane
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A convenient method for selective mono- and diiodination of alkyl aryl ethers by mercury(II) oxide-iodine reagent in dichloromethane is reported.
- Orito,Hatakeyama,Takeo,Suginome
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- Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes
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Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.
- Webster, Stacey,O'Rourke, Kerry M.,Fletcher, Conor,Pimlott, Sally L.,Sutherland, Andrew,Lee, Ai-Lan
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- Selective monoiodination of aromatic compounds with electrochemically generated I+ using micromixing
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Selective monoiodination of aromatic compounds such as dimethoxybenzene has been successfully achieved with I+, which is generated by anodic oxidation of I2 in acetonitrile, using micromixing. The Royal Society of Chemistry 2006.
- Midorikawa, Koji,Suga, Seiji,Yoshida, Jun-Ichi
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- A phase-dependent photoluminescent discotic liquid crystal bearing a graphdiyne substructure
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In recent years, graphdiyne and its derivatives with fascinating electro-optic properties have attracted tremendous scientific attention. Here we design and synthesize a graphdiyne-derived discotic liquid crystal material by decorating six wedge-shaped 3,
- Yu, Zhen,Chen, Xu-Man,Liu, Zhi-Yang,Wang, Meng,Huang, Shuai,Yang, Hong
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- Practical electrochemical iodination of aromatic compounds
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A practical method for electrochemical iodination of aromatic compounds was developed. The method involves the generation of I+ by electrochemical oxidation of I2 in CH3CN using H 2SO4 as supporting electrolyte followed by the reaction with aromatic compounds. The para/ortho selectivity for the reaction of mono-substituted benzenes was significantly improved using dimethoxyethane as cosolvent in the second step. The reaction with highly reactive aromatic compounds led to the formation of significant amounts of diiodo compounds in a macrobatch reactor. This problem was solved by fast 1:1 mixing of I+ with an aromatic compound using a microflow system consisting of a T-shaped micromixer and a microtube reactor.
- Kataoka, Kazuhide,Hagiwara, Yuji,Midorikawa, Koji,Suga, Seiji,Yoshida, Jun-Ichi
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- A method for preparing isothiaurea compounds based on substituted iodobenzene
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The present invention discloses a method for preparing isothiaurea compounds based on substituted iodobenzene, thiourea and substituted iodobenzene as a substrate, in the presence of metal hydrides, react in a solvent, and prepare isothiurea compounds. Is
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Paragraph 0017
(2021/12/07)
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- Synthesis of Fluorenes Starting from 2-Iodobiphenyls and CH2Br2 through Palladium-Catalyzed Dual C-C Bond Formation
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A facile and efficient approach is developed for the synthesis of fluorene and its derivatives starting from 2-iodobiphenyls and CH2Br2. A range of fluorene derivatives can be synthesized under relatively mild conditions. The reaction proceeds via a tandem palladium-catalyzed dual C-C bond formation sequence through the key dibenzopalladacyclopentadiene intermediates, which are obtained from 2-iodobiphenyls through palladium-catalyzed C-H activation.
- Shi, Guangfa,Chen, Dushen,Jiang, Hang,Zhang, Yu,Zhang, Yanghui
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supporting information
p. 2958 - 2961
(2016/07/06)
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- PROCESS FOR THE PREPARATION OF N-IODOAMIDES
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The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.
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Paragraph 00277-00278
(2015/05/26)
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- Halogen bonding of (iodoethynyl)benzene derivatives in solution
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Halogen bonding (XB) between (iodoethynyl)benzene donors and quinuclidine in benzene affords binding free enthalpies (δG, 298 K) between -1.1 and -2.4 kcal mol-1, with a strong LFER with the Hammett parameter σpara. The enthalpic dri
- Dumele, Oliver,Wu, Dino,Trapp, Nils,Goroff, Nancy,Diederich, Francois
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supporting information
p. 4722 - 4725
(2015/04/27)
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- Mild and selective organocatalytic iodination of activated aromatic compounds
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We describe an organocatalytic iodination of activated aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as the iodine source with thiourea catalysts in acetonitrile. The protocol is applicable to a number of aromatic substrates with significantly different steric and electronic properties. The iodination is generally highly regioselective and provides high yields of isolated products. NMR kinetic investigations conducted in THF-d 8indicate the role of sulfur in the thiourea motif as a nucleophile that is assisted by H-bonding in the key steps of the reaction. Georg Thieme Verlag Stuttgart . New York.
- Jakab, Gergely,Hosseini, Abolfazl,Hausmann, Heike,Schreiner, Peter R.
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p. 1635 - 1640
(2013/07/27)
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- Design and synthesis of a class of twin-chain amphiphiles for self-assembled monolayer-based electrochemical biosensor applications
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A new class of twin-chain hydroxyalkylthiols (mercaptoalkanols) is described that features a nearly constant cross section and the potential for modification at one or both termini. These compounds are regioselectively available through Pd-mediated coupli
- Fisher, Thomas J.,Canete, Socrates Jose P.,Lai, Rebecca Y.,Dussault, Patrick H.
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p. 3263 - 3270
(2013/07/05)
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- 5-METHOXY. 3'-OH UNBLOCKED, FAST PHOTOCLEAVABLE TERMINATING NUCLEOTIDES AND METHODS FOR NUCLEIC ACID SEQUENCING
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The present invention relates generally to 3'-OH unblocked nucleotides and nucleosides labeled and unlabeled with 5-methoxy-substituted nitrobenzyl-based photocleavable terminating groups for use in methods and systems related to DNA and RNA sequencing an
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Paragraph 91
(2013/03/28)
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- Regioselective synthesis of tetraalkynylarenes by consecutive dual sonogashira coupling reactions of the bis(triflate) of 4,5-diiodobenzene-1,2- diol
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The regioselective synthesis of nonsymmetric tetraalkynylarenes has been readily achieved through consecutive sets of Sonagashira cross-coupling reactions of the bis(triflate) derivative of 4,5-diiodobenzene-1,2-diol. The initial coupling reactions procee
- Fisher, Thomas J.,Dussault, Patrick H.
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experimental part
p. 2831 - 2836
(2012/07/01)
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- SELF-ASSEMBLED MONOLAYERS AND METHODS FOR USING THE SAME IN BIOSENSING APPLICATIONS
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Cross-linked amphiphile constructs that form self-assembled monolayers (SAMs) on metal surfaces such as gold surfaces are disclosed. These new SAMs generate well packed and highly oriented monolayer films on gold surfaces. A method for using the SAMs in t
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(2013/02/27)
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- Stereochemistry of benzylic carbon substitution coupled with ring modification of 2-nitrobenzyl groups as key determinants for fast-cleaving reversible terminators
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A complete set of 2-nitrobenzyl-modified reversible terminators have been developed, which upon exposure to UV light generate natural hydroxymethyl nucleotides (see scheme). The combination of a stereospecific (S)-tert-butyl group (R) at the benzylic carb
- Stupi, Brian P.,Li, Hong,Wang, Jinchun,Wu, Weidong,Morris, Sidney E.,Litosh, Vladislav A.,Muniz, Jesse,Hersh, Megan N.,Metzker, Michael L.
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supporting information; experimental part
p. 1724 - 1727
(2012/05/05)
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- Hypervalent iodine(III)-LiX combination in fluoroalcohol solvent for aromatic halogenation of electron-rich arenecarboxylic acids
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The novel reagent system, PhI(OAc)2-LiX combination in fluoroalcohol solvents, was found to be effective for halodecarboxylation of electron-rich arenecarboxylic acids. The method provided an efficient route to halogenated phenol ether derivatives. Georg Thieme Verlag Stuttgart ? New York.
- Hamamoto, Hiromi,Hattori, Sho,Takemaru, Kaori,Miki, Yasuyoshi
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scheme or table
p. 1563 - 1566
(2011/08/03)
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- FUSED AMINO PYRIDINE AS HSP90 INHIBITORS
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The present invention relates to HSP90 inhibitors containing fused amino pyridine core that are useful as inhibitors of HSP90 and their use in the treatment of HSP90 related diseases and disorders such as cancer, an autoimmune disease, or a neurodegenerative disease.
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- PROCESS FOR PRODUCING AROMATIC IODINE COMPOUND
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A process for producing an aromatic iodine compound. It has advantages of ease of handling and high safety. By the process, the reaction product having an excellent color tone can be produced in a high yield. The process for aromatic iodine compound production is characterized by introducing an aromatic compound and an active iodizing agent into a flow-through type reactor equipped with a high-speed mixer to continuously replace hydrogen atoms of the aromatic nucleus of the aromatic compound with iodine atoms.
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Page/Page column 16-17; 21; 23-24
(2008/06/13)
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- An efficient synthesis of 4,4′,5,5′-tetraiododibenzo-24-crown-8 and its highly conjugated derivatives
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4,4′,5,5′-Tetraiododibenzo-24-crown-8 (9), a practical building block, was prepared under efficient and mild reaction conditions starting from the simple starting material, catechol (1). Highly conjugated 4,4′,5,5′-tetraethynyldibenzo-24-crown-8 (10a,b) w
- Pak, Joshua J.,Mayo, Jaime L.,Shurdha, Endrit
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p. 233 - 237
(2007/10/03)
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- Bergman cyclopolymerization within the channels of functional hybrid nanocomposites formed by co-assembly of silica and polymerizable surfactant monomer
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The Bergman cyclopolymerization of polymerizable surfactant monomer was carried out within the hexagonal channels of functional hybrid nanocomposite formed by co-assembly with silica. The Royal Society of Chemistry 2006.
- Bhongale, Chetan Jagdish,Yang, Chung-He,Hsu, Chain-Shu
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p. 2274 - 2276
(2007/10/03)
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- 5-Exo-dig radical cyclization of enediynes: The first synthesis of tin-substituted benzofulvenes
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(Equation Presented) Bu3Sn-mediated 5-exo-dig radical cyclization of diaryl enediynes provides a mild and efficient approach to tin-substituted fulvenes. Further synthetic opportunities opened by this process and general factors responsible for
- Kovalenko, Serguei V.,Peabody, Scott,Manoharan, Mariappan,Clark, Ronald J.,Alabugin, Igor V.
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p. 2457 - 2460
(2007/10/03)
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- Synthesis, enantiomeric conformations, and stereodynamics of aromatic ortho-substituted disulfones
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Aromatic ortho-disulfone derivatives are readily accessible from diiodide precursors by CuI-mediated reaction with sodium sulfinate salts (DMF, 110°). The sulfonyl substituents adopt in solution and in the solid state two enantiomeric conformations (λ and δ) as evidenced by 31P- and IH-NMR data of the chiral D3-symmetric tris{4,5-bis[(4-methylphenyl)sulfonyl]benzene-1,2-diolato(2-)- κO,κO′}phosphate(v) anion (3a) and 1,2-bis(camphor-10-sulfonyl)-4,5-dimethoxybenzene((=1, 2-bis{{[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]- hept-1-y1]methyl}sulfonyl}-4,5-dimethoxybenzene; 6c). X-Ray structure analysis of 1,2-dimethoxy-4,5-bis(methylsulfonyl)benzene (6a) and 1,2-dimethoxy-4,5-bis(4-methylphenyl)sulfonyl]benzene (6b) confirmed in the solid state the preferred chiral orientation of the sulfonyl groups. Dynamic conformational isomerism was detected for 6c in its IH-NMR in the temperature range of 110°, the corresponding free energy being 19.8 kcal mol-1.
- Lacour, Jerome,Monchaud, David,Mareda, Jiri,Favarger, France,Bernardinelli, Gerald
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- Synthesis, enantiomeric conformations, and stereodynamics of aromatic orffto-substituted disulfones
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(equation presented) Aromatic ortho-disulfone derivatives are readily accessible from diiodide precursors by Cu(l)-mediated reactions with sodium sulfinate salts. The sulfone substituents adopt C2-symmetric enantiomeric conformations (λ and δ)
- Lacour, Jerome,Monchaud, David,Bernardinelli, Gerald,Favarger, France
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p. 1407 - 1410
(2007/10/03)
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- Synthesis and optical properties of novel unsymmetrical conjugated dendrimers
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The first unsymmetrical conjugated dendrimer was synthesized using a rather simple approach that involves only one synthon and two sets of reaction conditions. This dendrimer shows broad absorption in the UV and visible range and possesses an intrinsic en
- Peng, Zhonghua,Pan, Yongchun,Xu, Bubin,Zhang, Jianheng
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p. 6619 - 6623
(2007/10/03)
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- The direct iodination of arenes with chromium(VI) oxide as the oxidant
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An easy and cheap laboratory method is presented for the direct mono- and diiodination of a number of activated and deactivated arenes. The main iodination reactions occurred at the temperatures not exceeding 65°C for 0.5-12 h in the anhydrous, strongly acidic liquid system, I2/AcOH/Ac2O/H2SO4, in the presence of prior dissolved CrO3 used as the oxidant. The yields of the pure iodinated products varied from 31% (for 3,5- diiodobenzoic acid) up to 90% (for 4-iodoanisole). So far, benzonitrile and some oxidizable aromatics, e.g. naphthalene, fluorene, xanthene, and thiophene, have been found to be unsuitable for the effective iodination. Nevertheless, this novel, simple method of direct iodination is worthy to be extended to other appropriate aromatics.
- Lulinski, Piotr,Skulski, Lech
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p. 1665 - 1669
(2007/10/03)
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- Oxidation of Aromatic Compounds. III. Oxidation of Substituted Phenols and Their O-Derivatives in the System HSO3F-PbO2
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Low-temperature oxidation of substituted phenols and their O-derivatives in the system HSO3F-PbO2 involves intermediate formation of radical cations and dications.The reaction allows preparative syntheses of aryl fluorosulfonates, various benzyl alcohol derivatives, biaryls, and diarylmethanes with electron-acceptor substituents.
- Aver'yanov, S. F.,Rudenko, A. P.
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p. 1089 - 1098
(2007/10/03)
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- Preparation of N-Substituted Phthalimides by Palladium-Catalyzed Carbonylation and Coupling of o-Dihalo Aromatics and Primary Amines
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A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines.Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115 deg C, 90 psi of CO, 3 percent PdCl2L2, and 2.4 equiv of DBU.This process is tolerant of a wide variety of functional groups and gives good yields of the desired products.Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction.The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.
- Perry, Robert J.,Turner, S. Richard
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p. 6573 - 6579
(2007/10/02)
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- Iodination of Aromatic Ethers by Use of Benzyltrimethylammonium Dichloroiodate and Zinc Chloride
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The reaction of aromatic ethers with benzyltrimethylammonium dichloroiodate(1-) in acetic acid in the presence of zinc chloride at room temperature gave iodo-substituted aromatic ethers in good yields.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Watanabe, Masakazu,Fujisaki, Shizuo,Okamoto, Tsuyoshi
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p. 795 - 798
(2007/10/02)
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- Electron Transfer Mechanism for Periodic Acid Oxidation of Aromatic Substrates
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Evidence for the involvement of cation radicals during the periodic acid oxidation of aromatic substrates like hydrocarbons, phenolic ethers, phenols etc. has been presented.
- Bhatt, M. V.,Hosur, B. M.
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p. 1004 - 1005
(2007/10/02)
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