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Novel quinoline-based fluorescent bioimaging probe, KSNP117, for sentinel lymph node mapping
Fluorescent imaging agents with biocompatibility and high sensitivity are urgently required for the accurate detection of sentinel lymph nodes (SLNs). Herein, we report the design of a novel quinoline-based fluorescent probe, designated KSNP117, which can be applied as a biomedical imaging agent in the sensitive and quantitative detection of SLNs. KSNP117 exerted no adverse effects on the proliferation of ovary and immune cells and also showed excellent serum stability with photo-brightening effects.In vivofluorescent imaging revealed the accumulation of KSNP117 in the SLNs of nude mice within 10 min post injection, withoutin vivotoxicity, which was consistent with the findings ofex vivoimaging. These results support the potential of KSNP117 as a promising lymphatic tracer for biomedical imaging applications.
Cho, Sung Jin,Elbatrawy, Ahmed A.,Han, Ye Ri,Jeon, Hui-Jeon,Jeon, Yong Hyun,Kang, Kyung-Ku,Kim, Dong-Su,Kim, Kil Soo,Lee, Da Sol,Lee, Sang Bong,Lee, Sijoon,Nam, Ghilsoo,Sung, Soo-Eun
supporting information
p. 4857 - 4862
(2021/07/01)

Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination
We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.
Falk, Eric,Gasser, Valentina C. M.,Morandi, Bill
supporting information
p. 1422 - 1426
(2021/03/08)

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2
We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.
Zhang, Yanmeng,Zhang, He,Gao, Ke
supporting information
p. 8282 - 8286
(2021/10/25)

Efficient methylation of anilines with methanol catalysed by cyclometalated ruthenium complexes
Cyclometalated ruthenium complexes4-10allow the effective methylation of anilines with methanol to selectively giveN-methylanilines. This hydrogen autotransfer procedure proceeds under mild conditions (60 °C) in a practical manner (NaOH as base). Mechanistic investigations suggest an active homogenous ruthenium complex and β-hydride elimination of methanol as the rate determining step.
Piehl, Patrick,Amuso, Roberta,Spannenberg, Anke,Gabriele, Bartolo,Neumann, Helfried,Beller, Matthias
p. 2512 - 2517
(2021/04/22)

Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects
Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.
Huang, Shuang,Hong, Xi,Cui, He-Zhen,Zhan, Bing,Li, Zhi-Ming,Hou, Xiu-Feng
p. 3514 - 3523
(2020/10/09)

Selective N -monomethylation of primary anilines with the controllable installation of N -CH2D, N -CHD2, and N -CD3units
The selective N-monomethylation of primary anilines was realized by the use of the Me3N-BH3/N,N-dimethylformamide (DMF) system as the methyl source. This method also allows for the controllable introduction of N-CH2D, N-CHD2, and N-CD3 units with high lev
Meng, Jing,Wang, Yi-Feng,Wang, Zhijuan,Xia, Hui-Min,Xu, Ai-Qing,Zhang, Feng-Lian
supporting information
p. 4922 - 4926
(2020/07/30)

A novel DMSO-assisted regioselective iodination of aniline analogues
A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.
Bovonsombat, Pakorn,Lorpaiboon, Wanutcha,Laoboonchai, Sarocha,Sriprachaya-anunt, Prima,Yimkosol, Warangkana,Siriphatcharachaikul, Natthapatch,Siricharoensang, Pornpawit,Kangwannarakul, Terawee,Maeda, Jin,Losuwanakul, Satreerat,Mahesh Abhyankar, Maitraye
(2020/10/05)

Rh(III)-catalyzed N-nitroso-directed C-H olefination polymerization
Transition metal-catalyzed directed C-H functionalization promises a straightforward route to polymerization but remains highly underexplored. We report herein the development of a polymer synthesis protocol based on Rh(III)-catalyzed N-nitroso-directed C-H olefination reaction. The single bifunctional monomer approach allows the high-yield generation of polymers with relatively narrow PDI under mild conditions. Further convenient denitrosation transformation furnishes responsive fluorescent polymers with metal ion-selective quenching behaviors. The high Hg2+ selectivity observed in one system provides a handy enabling tool for detecting this hazardous species.
Liu, Zhongsu,Zeng, Hua,Zhang, Wenjing,Song, Chao,Yang, Fan,Liu, Yun,Zhu, Jin
p. 152 - 159
(2019/04/04)

Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines
The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.
Yao, Wubing,He, Lili,Han, Deman,Zhong, Aiguo
(2019/11/14)

Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines
The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.
Yao, Wubing,He, Lili,Han, Deman,Zhong, Aiguo
p. 14627 - 14635
(2019/12/02)

N -Methylation of ortho -substituted aromatic amines with methanol catalyzed by 2-arylbenzo [d] oxazole NHC-Ir(iii) complexes
Seven new chelated cyclometalated Ir complexes of ABON,P, ABON,O, and ABON,C(carbene) based on a rigid and tunable 2-arylbenzo[d]oxazole backbone have been prepared for the N-methylation of amines. Among these three coordinated modes, ABON,C(carbene)-chelated iridium-based catalysts exhibited good performance in the monomethylation of aromatic amines with methanol (MeOH) as the green methylation reagent. The steric-modified synthesis of ABON,C(carbene) complexes was described. The most active ABON,C(carbene) complex with marginal steric hindrance as a catalyst was obtained from the benzoxazole ring without a substituent and methyl group of the benzimidazole ring on the N-heterocyclic carbene (NHC) ligand. A variety of amines including para- and meta-substituted aromatic amines, as well as heterocyclic amines, were formulated as suitable substrates. Importantly, this catalyst considerably promoted the yield of the N-methylation of ortho-substituted aromatic amines. Controlled kinetic experiments and deuterium-labeling reactions of these ortho-substituted amines were conducted under optimized conditions. On the basis of the experimental results, a plausible mechanism was proposed.
Huang, Shuang,Hong, Xi,Cui, He-Zhen,Zhou, Quan,Lin, Yue-Jian,Hou, Xiu-Feng
p. 5072 - 5082
(2019/04/17)

Selective N-monomethylation of primary anilines with dimethyl carbonate in continuous flow
Selective N-monomethylation of anilines has been achieved under continuous flow conditions using dimethyl carbonate as a green methylating agent in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. Our methodology takes advantage of the expanded process windows available in the continuous flow regime to safely induce monomethylation in superheated solvents at high pressure. We propose selective N-monomethylation is achieved via an in situ protection-deprotection pathway, which is supported by the observed reactivities of several putative reaction intermediates. The robust and scalable method was applicable to a broad range of primary aniline substrates including ortho-, meta-, and para-substituted anilines, as well as electron-rich and electron-deficient anilines. The synthetic precursor of diazepam, 5-chloro-2-(methylamino)benzophenone, was selectively synthesized under our optimized conditions.
Seo, Hyowon,Bédard, Anne-Catherine,Chen, Willie P.,Hicklin, Robert W.,Alabugin, Alexander,Jamison, Timothy F.
p. 3124 - 3128
(2017/12/11)

Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol
An iron(0) complex bearing a cyclopentadienone ligand catalyzed N-methylation and N-ethylation of aryl and aliphatic amines with methanol or ethanol in mild and basic conditions through a hydrogen autotransfer borrowing process is reported. A broad range of aromatic and aliphatic amines underwent mono- or dimethylation in high yields. DFT calculations suggest molecular hydrogen acts not only as a reducing agent but also as an additive to displace thermodynamic equilibria.
Lator, Alexis,Gaillard, Sylvain,Poater, Albert,Renaud, Jean-Luc
supporting information
p. 5985 - 5990
(2018/10/02)

Design of "click" Fluorescent Labeled 2′-deoxyuridines via C5-[4-(2-Propynyl(methyl)amino)]phenyl Acetylene as a Universal Linker: Synthesis, Photophysical Properties, and Interaction with BSA
Microenvironment-sensitive fluorescent nucleosides present attractive advantages over single-emitting dyes for sensing inter-biomolecular interactions involving DNA. Herein, we report the rational design and synthesis of triazolyl push-pull fluorophore-la
Bag, Subhendu Sekhar,Gogoi, Hiranya
p. 7606 - 7621
(2018/06/18)

Tuning Lewis Acidity of Metal-Organic Frameworks via Perfluorination of Bridging Ligands: Spectroscopic, Theoretical, and Catalytic Studies
The Lewis acidity of metal-organic frameworks (MOFs) has attracted much research interest in recent years. We report here the development of two quantitative methods for determining the Lewis acidity of MOFs - based on electron paramagnetic resonance (EPR) spectroscopy of MOF-bound superoxide (O2?-) and fluorescence spectroscopy of MOF-bound N-methylacridone (NMA) - and a simple strategy that significantly enhances MOF Lewis acidity through ligand perfluorination. Two new perfluorinated MOFs, Zr6-fBDC and Zr6-fBPDC, where H2fBDC is 2,3,5,6-tetrafluoro-1,4-benzenedicarboxylic acid and H2fBPDC is 2,2′,3,3′,5,5′,6,6′-octafluoro-4,4′-biphenyldicarboxylic acid, were shown to be significantly more Lewis acidic than nonsubstituted UiO-66 and UiO-67 as well as the nitrated MOFs Zr6-BDC-NO2 and Zr6-BPDC-(NO2)2. Zr6-fBDC was shown to be a highly active single-site solid Lewis acid catalyst for Diels-Alder and arene C-H iodination reactions. Thus, this work establishes the important role of ligand perfluorination in enhancing MOF Lewis acidity and the potential of designing highly Lewis acidic MOFs for fine chemical synthesis.
Ji, Pengfei,Drake, Tasha,Murakami, Akiko,Oliveres, Pau,Skone, Jonathan H.,Lin, Wenbin
supporting information
p. 10553 - 10561
(2018/08/03)

Novel nonmetal catalytic bidirectional selective reduction method of tertiary aromatic amide
The invention relates to a novel effective bidirectional selective environment-friendly method for hydrosilation reduction of tertiary aromatic amide and an organic silicon reagent. The method comprises the following steps: selecting a nonmetal catalytic system, and selectively preparing a secondary or tertiary organic amine compound by successively catalyzing tertiary aromatic amide and cheap PHMS or triethoxysilane under a mild condition. By adopting the method, the bidirectional selective reduction of the tertiary aromatic amide is realized by innovatively utilizing an electronic effect and steric hindrance difference of an organic silicon reagent at first time, so that a brand new strategy is provided for the reduction of amide and derivative of the amide, the defects of the traditional method that the substrate functional group is poor in compatibility, the production cost is high and the like can be overcome, and the application prospect of the amine compound prepared in industrial production or laboratory is promising.
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Paragraph 0034; 0035; 0036; 0037

(2017/10/22)

Thermolysis and radiofluorination of diaryliodonium salts derived from anilines
Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.
Linstad, Ethan J.,Vāvere, Amy L.,Hu, Bao,Kempinger, Jayson J.,Snyder, Scott E.,DiMagno, Stephen G.
supporting information
p. 2246 - 2252
(2017/03/17)

Mono-N-methylation of anilines with methanol catalyzed by a manganese pincer-complex
The selective mono-N-methylation of anilines derivatives was achieved under mild conditions using inexpensive methanol as C1 source. Under hydrogen borrowing conditions, using a tridentate PN3P manganese pre-catalyst (5?mol%), a catalytic amount of base (20?mol%), for 24?h at 120?°C, a large variety of anilines derivatives was methylated in good to excellent yield. Mechanistic investigations allowed us to isolate and characterize by X-ray diffraction studies a de-aromatized manganese intermediate.
Bruneau-Voisine, Antoine,Wang, Ding,Dorcet, Vincent,Roisnel, Thierry,Darcel, Christophe,Sortais, Jean-Baptiste
p. 57 - 62
(2017/02/13)

Ω-and its manufacturing method perfluoroalkyl substd. imidating monoiodo
PROBLEM TO BE SOLVED: To provide a novel compound of a fluorine-containing polyether compound, on both terminals of which reaction sites crosslinkable with an organic peroxide can be formed. SOLUTION: An ω-iodoperfluoroalkyl-substituted aniline derivative represented by formula (1), wherein R1is a hydrogen atom or a 1-3C alkyl group; and n is an integer of 4 to 10, is produced by: coupling reacting a halogenoacetoanilido whose halogen group is an iodine group or a bromine group or a N-monoalkyl-substituted substance thereof with a 1-3C alkyl group as a substituent, with a ω,ω'-diiodoperfluoroalkane compound having a 4-10C perfluoroalkylene group; and thereafter hydrolyzing the reaction product. COPYRIGHT: (C)2013,JPOandINPIT
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Paragraph 0025

(2019/12/28)

Base-oxidant promoted metal-free N-demethylation of arylamines
A metal-free oxidative N-demethylation of arylamines with triethylamine as a base and tert-butyl hydroperoxide (TBHP) as oxidant is reported in this paper. The reaction is general, practical, inexpensive, non-toxic, and the method followed is environmentally benign, with moderate to good yields. [Figure not available: see fulltext.]
Botla, Vinayak,Barreddi, Chiranjeevi,Daggupati, Ramana V,Malapaka, Chandrasekharam
p. 1469 - 1473
(2016/09/19)

Efficient ruthenium-catalyzed N-methylation of amines using methanol
An in situ-generated complex from [RuCpCl2]2 and dpePhos ligand is reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst system provides selective N-monomethylation of substituted primary anilines and sulfonamides as well as N,N dimethylation of primary aliphatic amines in excellent yields at 40-100 °C with good tolerance to reducible functional groups. The catalytic intermediate CpRu(dpePhos)H was isolated and was shown to be active for methylation in the absence of base.
Dang, Tuan Thanh,Ramalingam, Balamurugan,Seayad, Abdul Majeed
p. 4082 - 4088
(2015/11/11)

Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions
1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.
Alikarami, Mohammad,Nazarzadeh, Somayeh,Soleiman-Beigi, Mohammad
p. 157 - 162
(2015/01/30)

Discovery, synthesis, and biological evaluation of thiazoloquin(az)olin(on)es as potent CD38 inhibitors
A series of thiazoloquin(az)olinones were synthesized and found to have potent inhibitory activity against CD38. Several of these compounds were also shown to have good pharmacokinetic properties and demonstrated the ability to elevate NAD levels in plasm
Haffner, Curt D.,Becherer, J. David,Boros, Eric E.,Cadilla, Rodolfo,Carpenter, Tiffany,Cowan, David,Deaton, David N.,Guo, Yu,Harrington, Wallace,Henke, Brad R.,Jeune, Michael R.,Kaldor, Istvan,Milliken, Naphtali,Petrov, Kim G.,Preugschat, Frank,Schulte, Christie,Shearer, Barry G.,Shearer, Todd,Smalley, Terrence L.,Stewart, Eugene L.,Stuart, J. Darren,Ulrich, John C.
p. 3548 - 3571
(2015/05/05)

Direct condensation of functionalized sp3 carbons with formanilides for enamine synthesis using an in situ generated HMDS amide catalyst
The efficient synthesis of functionalized enamines including β-enaminoesters was effectively accomplished by the direct condensation of functionalized sp3 carbanions such as acetates with formamides using in situ generated HMDS base from catalytic cesium fluoride and stoichiometric tristrimethylsilylamine. This journal is the Partner Organisations 2014.
Taneda, Hiroshi,Inamoto, Kiyofumi,Kondo, Yoshinori
supporting information
p. 6523 - 6525
(2014/06/09)

General and efficient method for direct N-monomethylation of aromatic primary amines with methanol
The direct N-monomethylation of aromatic primary amines, including arylamines, arylsulfonamides and amino-azoles, using methanol as a methylating agent has been accomplished in the presence of a [CpIrCl2]2/NaOH system. From both synthetic and environmental points of view, the reaction is highly attractive because of low catalyst loading, broad substrate scope and excellent selectivities.
Li, Feng,Xie, Jianjiang,Shan, Haixia,Sun, Chunlou,Chen, Lin
p. 8645 - 8652
(2015/03/05)

Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene
Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.
Shen, Hao,Vollhardt, K. Peter C.
supporting information; experimental part
p. 208 - 214
(2012/03/11)

A useful and convenient synthetic protocol for iodination of organic substrates using a combination of vanadyl acetylacetonate, hydrogen peroxide, and sodium iodide
A wide variety of organic substrates can be iodinated selectively in good yields by employing a combination of vanadyl acetylacetonate, hydrogen peroxide, and sodium iodide at ice-bath temperature. Good yield, selectivity, use of cost effective reagents, and mild and environmentally benign reaction conditions are some of the major advantages of this protocol.
Khan, Abu T.,Ali, Shahzad
p. 1239 - 1243
(2013/01/15)

P-Iodinations in hydrocarbon media: Continuous flow reactor application
Regiospecific iodination of aryl amines, that is, aryl compounds possessing strong electron donating groups (EDG's) in the p-position, is described. This procedure features not only the unique use of hydrocarbon media for such substitutions but also the absence of any oxidants aside from iodine itself. Further potential of this hydrocarbon media based electrophilic aromatic substitution is demonstrated by the coupling of the iodination with an in situ halogen/lithium exchange and product forming nucleophilic addition in a batch process. The protocol was ultimately scaled to a continuous flow reactor using an isolated p-iodoarylamine. Constituted as described, these procedures possess enhanced atom-economical, green and safety aspects compared to existing literature protocols.
Slocum,Tekin, Kristen C.,Nguyen, Quang,Whitley, Paul E.,Reinscheld, Thomas K.,Fouzia, Begum
experimental part
p. 7141 - 7145
(2012/01/05)

Iodination of anilines and phenols with 18-crown-6 supported ICl 2-
A highly crystalline iodinating reagent, {[K·18-C-6]ICl 2}n, was synthesized in high yield (93%). The trihalide is supported by an 18-crown-6 macrocycle and forms a coordination polymer in the solid state. This reagent iodinates anilines and phenols efficiently under mild conditions. Controlled mono-iodination with anilines was easily achieved while poly-iodination was observed with phenols.
Mbatia, Hannah W.,Ulloa, Olbelina A.,Kennedy, Daniel P.,Incarvito, Christopher D.,Burdette, Shawn C.
experimental part
p. 2987 - 2991
(2011/06/16)

1,7-palladium migration via C-H activation, followed by intramolecular amination: Regioselective synthesis of benzotriazoles
A novel 1,7-palladiummigration-cyclization-dealkylation sequence for the regioselective synthesis of benzotriazoles has been developed. These reactions proceed in excellent yields with high regioselectivities. The mechanism of the reaction has also been investigated.
Zhou, Jun,He, Jianjun,Wang, Binjie,Yang, Weijun,Ren, Hongjun
supporting information; experimental part
p. 6868 - 6870
(2011/06/21)

Selective iodination of some phenols, anilines and methoxyarenes by molecular iodine in the presence of 1-butyl-3-methylimidazolium hydrogen sulphate
A simple, mild and regioselective method for the iodination of some phenols, anilines and methoxyarenes by using molecular iodine in presence of 1-butyl-3-methylimidazolium hydrogen sulphate ([bmim]-HSO4) in acetonitrile as solvent is reported. One-pot synthesis, mild reaction conditions, short reaction times and excellent yields of the products are noteworthy.
Tajik, Hassan,Parsa, Fatemeh
experimental part
p. 465 - 466
(2011/10/19)

5-(Dimethylamino)-N-(4-ethynylphenyl)-1-naphthalenesulfonamide as a novel bifunctional antitumor agent and two-photon induced bio-imaging probe
A novel compound, (5-(dimethylamino)-N-(4-ethynylphenyl)-1- naphthalenesulfonamide), was prepared and characterized; it shows dual functional roles as an effective antitumor and a two-photon induced bio-imaging agent.
Chui,Wang,Chow,Yuen,Wong,Kwok,Cheng,Wong,Tong,Chan,Lau,Lai,Lam,Fabbri,Tao,Gambari,Wong
supporting information; experimental part
p. 3538 - 3540
(2010/08/07)

Gold or no gold: One-pot synthesis of tetrahydrobenz[b]azepin-4-ones from tertiary n-(but-3-ynyl)anilines
Depending on the tertiary aniline substrates, an efficient, one-pot synthesis of tetrahydrobenz[b]azepin-4-ones needs either gold catalysts or no catalyst at all. In the reaction, the aniline nitrogen plays a unique role in relaying "O" from m-CPBA to a tethered C-C triple bond, which is inert to the oxidant under the mild reaction conditions.
Cui, Li,Zhang, Guozhu,Peng, Yu,Zhang, Liming
supporting information; experimental part
p. 1225 - 1228
(2009/08/07)

Direct halogenation of organic compounds with halides using oxone in water - A green protocol
Direct bromination and iodination of various aromatic compounds with NaBr and NaI using oxone (2KHSO5·KHSO4·K 2S04) in water was accomplished successfully in high-to-excellent yields. The main benefit of this protocol is the performance of the reactions in water in the presence of a harmless oxidant without the use of any organic cosolvents. Using NaBr and NaI as the safe sources of halogens is another advantage of the protocol. This method is easily applicable to the large-scale operations. We have also applied this method successfully for the iodocyclization of an unsaturated alcohol and an unsaturated carboxylic acid.
Firouzabadi,Iranpoor,Kazemi
experimental part
p. 1675 - 1681
(2010/01/29)

Highly efficient halogenation of organic compounds with halides catalyzed by cerium(III) chloride heptahydrate using hydrogen peroxide as the terminal oxidant in water
In this article a new environmentally friendly catalytic method is described for the efficient monoiodination and bromination of arenes and also iodoetherification and iodolactonization of olefins using hydrogen peroxide as the terminal oxidant. The method is based on using sodium iodide or sodium bromide, hydrogen peroxide (35%) and cerium(III) chloride as an effective catalyst in water at room temperature or under reflux conditions. By this protocol, iodination of anilines proceeded with high regioselectivity at the para position with the formation of small amounts of the ortho isomers. However, bromination of anilines proceeded with absolute regioselectivity to give the para isomers as the sole products in high yields. Iodinations and bromi-nations of m-xylene, toluene, chloro- and bromobenzenes were proceeded with excellent regioselectivity to produce the para isomers as the sole products. Benzene was also halogenated by this catalytic system to give the monohalogenated benzene in good yields. Iodoetherification and iodolactonization of olefins also proceeded easily in high yields at room temperature. However, the bromination of olefins by this protocol failed and the starting materials were detected intact.
Firouzabadi, Habib,Iranpoor, Nasser,Kazemi, Somayeh,Ghaderi, Arash,Garzan, Atefeh
experimental part
p. 1925 - 1932
(2011/03/18)

Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors
The present application describes sulfonylaminovalerolactams and derivatives thereof of Formula I: or pharmaceutically acceptable salt forms thereof, wherein ring G is a mono- or bicyclic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.
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(2008/06/13)

Microwave-accelerated or conventionally heated iodination reactions of some aromatic amines, using ortho-periodic acid as the oxidant
A fast and simple method for the oxidative iodination of some aromatic amines, either under microwave irradiation or conventional heating, is reported, using diiodine and ortho-periodic acid as the oxidant. The reactions were carried out in boiling CH2Cl2 solutions under a reflux condenser. For the microwave assisted reactions, the reaction times were always notably shortened, but the yields were usually less influenced as compared with the conventional method.
Sosnowski, Maciej,Skulski, Lech,Wolowik, Katarzyna
p. 617 - 621
(2007/10/03)

Eco-friendly Oxidative Iodination of Various Arenes with a Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant
Three easy eco-friendly laboratory procedures are presented for the oxidative iodination of various activated and deactivated arenes with molecular iodine, in the presence of UHP (percarbamide), a stable, strongly H-bonded, solid urea-hydrogen peroxide adduct as the oxidant.
Lulinski, Piotr,Kryska, Anna,Sosnowski, Maciej,Skulski, Lech
p. 441 - 445
(2007/10/03)

Synthesis and properties of a ROMP backbone polymer with efficient, laterally appended nonlinear optical chromophores
The synthesis and properties of a new ROMP backbone polymer bearing lateral donor-acceptor-substituted (E)-diethynylethene ((E)-hex-3-ene-1,5-diyne) chromophores are described. The polymer with an average of 40 monomeric repeat units is readily soluble in common organic solvents such as tetrahydrofuran, dichloromethane and chloroform. Good optical-quality films were obtained by spin coating. The third-order susceptibility χ(3) at a wavelength of 1907 nm was determined to be 100 times greater than that of fused silica. After electrical poling, the polymer also showed a significant second-order nonlinear optical coefficient (d33) value, which decays by a factor of two over a period of one month at room temperature.
Raimundo, Jean-Manuel,Lecomte, Steve,Edelmann, Michael J.,Concilio, Simona,Biaggio, Ivan,Bosshard, Christian,Guenter, Peter,Diederich, Francois
p. 292 - 295
(2007/10/03)

Selective para-iodination of methoxyarenes, phenols, and anilines with iodine in the presence of poly (4-vinylpyridine)-supported peroxodisulfate
A mild and efficient method for the direct iodination of methoxyarenes, phenols, and anilines using iodine and poly (4-vinylpyridine)-supported peroxodisulfate in acetonitrile solution, is presented. Selective para-substitution and also, the rather general applicability of this system is the advantage of the method.
Tajik, Hassan,Mohammadpoor-Baltork, Iraj,Rasht-Abadi, Hassan Rafiee
p. 3579 - 3585
(2007/10/03)

Low loss electro-optic polymers and devices made therefrom
The synthesis of novel, high μβ electro-optical chromophores is described. These chromophores are polymerizable with a host polymer or copolymer. The chromophore polymerizable groups comprise epoxy, thioepoxy, oxetane and thiooxetane material which undergo a ring opening polymerization reaction in the presence of a cationic photoinitiator and actinic radiation. The high μβ chromophores, mixed with a selected host polymer, copolymer, oligomer, or one or a plurality of polymerizable monomers, can be used to prepare optical waveguides and other optical elements and/or devices. The electro-optical chromophores of the invention can be used as a replacement for LiNbO3 in the formation of electro-optical devices, particularly electro-optical modulators.
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Page/Page column 4-5

(2010/01/31)

Microwave-accelerated iodination of some aromatic amines, using urea-hydrogen peroxide addition compound (UHP) as the oxidant
A fast and simple method for the oxidative iodination of some aromatic amines, under microwave irradiation, is reported, using diiodine and the the strongly H-bonded urea-hydrogen peroxide addition compound (H 2NCONH)2...H2O2, UHP) as the oxidant. The reactions were carried out in boiling CHCl3 under a reflux condenser to afford, within 10 minutes, the purified monoiodinated products in 40-80% yields.
Sosnowski, Maciej,Skulski, Lech
p. 867 - 870
(2007/10/03)

Benzyltriethylammonium dichloroiodate/sodium bicarbonate combination as an inexpensive, environmentally friendly, and mild iodinating reagent for anilines
(matrix presented) Monoiodinated anilines were prepared in good to excellent yields by the action of benzyltriethylammonium dichloroioadate on anilines in the presence of sodium bicarbonate and methanol. The iodinating reagent was prepared in an environmentally friendly fashion without the use of organic solvents.
Kosynkin, Dmitry V.,Tour, James M.
p. 991 - 992
(2007/10/03)

Iodination with Potassium Permanganate/Hydroiodic Acid/Acetonitrile Reagent
Iodination of various aromatic amines proceeds smoothly with a preformed homogeneous mixture of hydroiodic acid potassium permanganate in acetonitrile. para-Substituted products were obtained in high yields (71-78%) within twelve hours at room temperature. With a slight modification of the permanganate, hydroiodic acid and substrate ratio, iodination of alkynes to vic-diiodoalkenes can be carried out at 60 °C in 65-87% yield.
Chen, Jyh-An,Lin, Ching-Shan,Liu, Lilian Kao
p. 95 - 99
(2007/10/03)

Aromatic iodination with the I2-HgX2 combination
The reaction of differnt aromatic compounds 1a-1t with iodine and a mercury(II)-salt 2 [mercury(II) chloride, nitrate or triflate] (1:1:1 molar ratio) in dichloromethane at room temperature leads to the corresponding iodoarene 3, the obtained regiochemistry being the expected. Concerning the mercury(II) salt, the observed reactivity decreased in the series triflate > nitrate > chloride according to their ionic character. An activation of the iodine molecule by the mercury(II) salt followed by a S(E) reaction with the aromatic compounds is postulated as the possible mechanism.
Bachki, Abderrazak,Foubelo, Francisco,Yus, Miguel
p. 5139 - 5146
(2007/10/02)

SULPHONAMIDE DERIVATIVES
The invention concerns sulphonamide derivatives of the formula I wherein R1 includes (1-4C)alkyl; R2 and R3 together form ?A2 ?X2 ?A3? which defines a ring having 5 to 7 ring atoms, wherein A2 and A3 each is (1-3 C)alkylene and X2 is oxy, thio, sulphinyl or sulphonyl; A1 is a direct link to X1 or is (1-3 C)alkylene; X1 is oxy, thio, sulphinyl, sulphonyl or imino; Ar is optionally substituted phenylene or Ar is pyridylene; Q is nitrogen or of the formula CR7, wherein R7 includes hydrogen, halogeno, (1-4 C)alkyl and (1-4 C)alkoxy; each of R4 and R5 is (1-4 C)alkyl, (3-4 C)alkenyl, (3-4 C)alkynyl or optionally substituted phenyl, benzyl or pyridyl, or R5 may be hydrogen; and R6 has any of the meanings defined for R7; or a pharmaceutically-acceptable salt thereof; processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors
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(2008/06/13)

Halogenation Using Quaternary Ammonium Polyhalides. VII. Iodination of Aromatic Amines by Use of Benzyltrimethylammonium Dichloroiodate(1-)
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
p. 600 - 602
(2007/10/02)

Synthesis of Some Substituted Dimethyl and Diethyl 4-(Phenylethynyl)-2,6-pyridinedicarboxylates
Substituted dimethyl and diethyl 4-(phenylethynyl)-2,6-pyridinedicarboxylates were prepared by coupling reactions between dialkyl 4-halo-2,6-pyridinedicarboxylates and terminal arylacetylenes in the presence of an organopalladium catalyst and copper(I) iodide in a suitable solvent system.The terminal acetylenes needed in this work were synthesized from the corresponding aryl halides using either (trimethylsilyl)acetylene or 2-methyl-3-butyn-2-ol followed by deprotection of the triple bond, depending on the nature of the compound in question.
Takalo, Harri,Kankare, Jouko,Haenninen, Elina
p. 448 - 454
(2007/10/02)

A HIGHLY EFFICIENT AND GENERAL N-MONOMETHYLATION OF FUNCTIONALIZED PRIMARY AMINES VIA FORMYLATION -- BORANE:METHYL SULFIDE REDUCTION
Formylation of functionalized primary aromatic and aliphatic amines with acetic formic anhydride (AFA) followed by borane:methyl sulfide reduction in the same pot affords the corresponding N-methylamines in excellent isolated yields, uncontaminated by bis alkylation; the reaction sequence is applicable to even very weakly basic and sterically hindered amines.
Krishnamurthy, S.
p. 3315 - 3318
(2007/10/02)