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Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes
The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.
Cloutier, Mélissa,Roudias, Majdouline,Paquin, Jean-Fran?ois
supporting information
p. 3866 - 3870
(2019/05/24)

SPIRO-CONTAINING PLATINUM (II) EMITTERS WITH TUNABLE EMISSION ENERGIES AND SYNTHESES THEREOF
An asymmetric tetradentate metal complex of a N^C^C^N comprising tetradentate ligand has a metal connected to binding sites which are connected to each other via three or four covalent bonds that can be either single or double bonds with bridging linkers reside between C^C and C^N moieties. These linkers result in three-dimension metal complexes with distorted square planar geometries. The four donor atoms coordinate to a metal center. Upon metal binding a 5-6-6 membered metallocycle is formed upon chelation including a first nitrogen donor bond, a first metal-carbon bond, a second metal-carbon bond, and a second nitrogen donor bond. The light emission from these metal complexes can be tuned by the ligand structure over the entire visible spectrum.
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(2019/08/12)

Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives
A palladium-catalyzed benzoquinone C-H functionalization/ cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2, 3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.
Ichake, Sachin S.,Konala, Ashok,Kavala, Veerababurao,Kuo, Chun-Wei,Yao, Ching-Fa
supporting information
p. 54 - 57
(2017/11/28)

Reaction discovery using acetylene gas as the chemical feedstock accelerated by the stop-flow micro-tubing reactor system
Acetylene gas has been applied as a feedstock under transition-metal catalysis and photo-redox conditions to produce important chemicals including terminal alkynes, fulvenes, and fluorinated styrene compounds. The reaction discovery process was accelerated through the use of stop-flow micro-tubing reactors. This reactor prototype was developed by joining elements from both continuous micro-flow and conventional batch reactors, which was convenient and effective for gas/liquid reaction screening. Notably, the developed transformations were either inefficient or unsuccessful in conventional batch reactors. Its success relies on the unique advantages provided by this stop-flow micro-tubing reactor system.
Xue, Fei,Deng, Hongping,Xue, Chengwen,Mohamed, Dara Khairunnisa Binte,Tang, Karen Yuanting,Wu, Jie
p. 3623 - 3627
(2017/07/11)

Control of the Regioselectivity in Cobalt- versus Ruthenium-Catalyzed Alder-ene Reaction of Unsymmetrical 1,3-Diynes
The Alder-ene reaction of trialkylsilyl-substituted 1,3-butadiynes with terminal alkenes was investigated utilizing a cobalt-based catalyst, and the results were compared with Alder-ene rections catalyzed by the [CpRu(H3CCN)3]PF6 catalyst. Obviously, the two catalysts gave complementary results of yn-dienes differing in the site where the new carbon-carbon bond was formed. Of particular interest are observations concerning the double bond migration within the alkene component. While simple alkenes gave exclusively the E-configuration, the application of 3-buten-1-ol resulted in the corresponding Z-double bond, indicating that the hydroxyl group acts as donor coordinating to the cobalt center and thereby altering the reaction pathway.
Weber, Sebastian M.,Hilt, Gerhard
supporting information
p. 564 - 567
(2017/02/10)

Enantioselective synthesis of β-fluoro-β-aryl-α-aminopentenamides by organocatalytic [2,3]-sigmatropic rearrangement
The tetramisole-promoted catalytic enantioselective [2,3]-sigmatropic rearrangement of quaternary ammonium salts bearing a (Z)-3-fluoro-3-arylprop-2-ene group generates, after addition of benzylamine, a range of β-fluoro-β-aryl-α-aminopentenamides containing a stereogenic tertiary fluorine substituent. Cyclic and acyclic nitrogen substituents as well as various aromatic substituents are tolerated, giving the β-fluoro-β-aryl-α-aminopentenamide products in up to 76% yield, 96:4 dr, and 98:2 er.
Kasten, Kevin,Slawin, Alexandra M. Z.,Smith, Andrew D.
p. 5182 - 5185
(2017/11/06)

A mild preparation of alkynes from alkenyl triflates
We report herein a protocol for preparing alkynes from alkenyl triflates. Stoichiometric LiCl promotes this transformation in DMF at ambient temperature. A range of terminal and internal alkynes were obtained smoothly. A one-pot procedure of alkyne format
Yang, Xiaowen,Wu, Dimin,Lu, Zhaohong,Sun, Hongbin,Li, Ang
supporting information
p. 5591 - 5594
(2016/07/06)

Efficient synthesis of N-arylsulfonyl-1,2,3-triazoles from 1,1-dibromo-2-arylethylenes
N-arylsulfonyl-1,2,3-triazoles were synthesized from 1,1-dibromo-2-arylethylenes via a one-pot reaction involving the Cs2CO3-mediated dehydrobromination process of the dibromoalkenes to produce alkynes followed by the Cu(I)-catalyzed Huisgen cycloaddition of the alkyne intermediates with tosyl azide.
Xu, Wenjing,Zhang, Wensheng,Zhang, Fei
p. 165 - 167
(2016/07/06)

An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin
An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.
Liu, Shihui,Chen, Xiaobei,Hu, Yanwei,Yuan, Laiqi,Chen, Shaohua,Wu, Ping,Wang, Wei,Zhang, Shilei,Zhang, Wei
p. 553 - 560
(2015/03/05)

Synthesis and evaluation of aminopyridine derivatives as potential BACE1 inhibitors
To identify a new non-peptidyl BACE1 inhibitor, we focused on the aminopyridine structure, which binds to the active sites of BACE1. Synthesis of aminopyridine derivatives and evaluation of inhibitory activity against rBACE1 are described. The 2-aminopyri
Konno, Hiroyuki,Sato, Taki,Saito, Yugo,Sakamoto, Iori,Akaji, Kenichi
supporting information
p. 5127 - 5132
(2015/11/09)

Visible-Light-Promoted Vinylation of Tetrahydrofuran with Alkynes through Direct C-H Bond Functionalization
(Chemical Equation Presented) Mild and direct C-H bond functionalizations and vinylations of tetrahydrofuran with alkynes have been accomplished through visible light photocatalysis, yielding a range of vinyl tetrahydrofurans under the synergistic actions of organic dye-type photocatalyst eosin Y, tert-butyl hydroperoxide (t-BuOOH), and a 45 W household lightbulb. A significant kinetic isotope effect (KIE) was recorded, which helps shed light on the mechanistic course.
Li, Jing,Zhang, Jing,Tan, Haibo,Wang, David Zhigang
p. 2522 - 2525
(2015/05/27)

Ortho-Carboranylphenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity and heat shock protein (HSP) 60 chaperon activity
ortho-Carboranylphenoxy derivatives were synthesized and evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, compound 1d showed the most significant
Li, Guangzhe,Azuma, Soyoko,Sato, Shinichi,Minegishi, Hidemitsu,Nakamura, Hiroyuki
p. 2624 - 2628
(2015/06/08)

Pseudo five-component synthesis of 3-(hetero)arylmethyl-2,5-di(hetero)-aryl-substituted thiophenes via sonogashira-glaser cyclization sequence
The Sonogashira-Glaser sequence combined with a microwave-assisted cyclization is a powerful tool to synthesize unsymmetrically substituted conjugated thiophenes. A variety of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes could be synthesized in moderate to excellent yields using a single Pd/Cu catalyst system. The presented method is strikingly simple to perform using commercially available starting materials. The obtained trisubstituted oligothiophene derivatives are interesting molecules for materials science.
Klukas, Fabian,Perkampus, J?rg,Urselmann, Dominik,Müller, Thomas J. J.
p. 3415 - 3422
(2015/02/02)

Autotandem catalysis: Synthesis of pyrroles by gold-catalyzed cascade reaction
A novel synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction has been developed. The reaction proceeded with an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety and was followed by gold-catalyzed 5-endo-dig cyclization and aromatization. Gold catalysts play a dual role in activating nucleophilicity or electrophilicity of terminal acetylenes by forming gold-acetylides or by π-coordination. The formal (3 + 2) annulation of two components provided a variety of substituted pyrroles in a modular fashion.
Ueda, Hirofumi,Yamaguchi, Minami,Kameya, Hiroshi,Sugimoto, Kenji,Tokuyama, Hidetoshi
p. 4948 - 4951
(2015/04/27)

Catalytic cascade hydroalkoxylation/isomerization/[4 + 2] cycloaddition using enyne alcohols as latent dienes or dienophiles
Enyne alcohols can react as precursors of either dienes or dienophiles with different substrates after hydroxylation and isomerization by gold catalysis. As such, oxa-bridged tricyclo[5.2.2.02,6]undec-8-ene-3,5-dione derivatives have been obtained by the Diels-Alder reaction and tetrahydro-1H-furo[3,4-c]pyran derivatives could be accessed by the hetero-Diels-Alder cycloaddition.
Guo, Rui,Li, Kang-Nan,Gong, Liu-Zhu
supporting information
p. 6707 - 6712
(2013/10/01)

Synthesis, DNA-binding abilities and anticancer activities of triazole-pyrrolo[2,1-c][1,4]benzodiazepines hybrid scaffolds
We synthesized a new series of PBD-hybrid derivatives having tethered triazoles and investigated for their cytotoxicity. The studies indicated that cis-olefin compounds induce higher cytotoxicity with increase in the G1 cell cycle phase compared with the trans-compounds. Quantitative RT-PCR assay indicated that compounds (16a-d) induced G1 phase arrest through down-regulation of cyclin D1 and up-regulation of p21, p27, and p53 mRNA expressions. Compounds 16a-d induced A375 early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide. Moreover, the Western blot analysis showed that A375 treated by compounds (16a-d) resulted in decreased levels of Bcl-2 and Bcl-xL, increased levels of Bax and Bad, and caspase/PARP degradation to identify apoptotic cells.
Chen, Chung-Yu,Lee, Pei-Hua,Lin, Yong-Yong,Yu, Wen-Ting,Hu, Wan-Ping,Hsu, Chia-Chen,Lin, Ying-Ting,Chang, Long-Sen,Hsiao, Cheng-Tien,Wang, Jeh-Jeng,Chung, Mei-Ing
p. 6854 - 6859
(2014/01/06)

Cs2CO3-mediated synthesis of terminal alkynes from 1,1-dibromo-1-alkenes
An unprecedented route to prepare terminal alkynes from 1,1-dibromo-1-alkenes mediated by Cs2CO3 was proven. 1,1-Dibromo-1-alkenes bearing various functional groups were efficiently converted to corresponding terminal alkynes in moderate to excellent yields.
Zhao, Ming,Kuang, Chunxiang,Yang, Qing,Cheng, Xuezhi
scheme or table
p. 992 - 994
(2011/03/22)

Synthesis of indene derivatives via electrophilic cyclization
3-Iodo-1H-indene derivatives are synthesized by iodonium-promoted 5-endo-dig carbocyclization of 2-substituted ethynylmalonates. Various 2-substituted ethynylmalonates bearing aryl-, alkyl-and ether-protected propargyl alcohols were successfully converted
Khan, Zulfiqar Ali,Wirth, Thomas
supporting information; experimental part
p. 229 - 231
(2009/06/20)

Thieme Chemistry Journal Awardees - Where are they now? A general one-step synthesis of alkynes from enolisable carbonyl compounds
Terminal and internal acetylenes were obtained in good to excellent isolated yields from carbonyl compounds by converting the carbonyl functionality into the enol nonaflate intermediate followed by elimination to give the C-C triple bond. The one-pot transformations were uniformly induced by phosphazene bases combined with mildly electrophilic nonafluorobutane-1-sulfonyl fluoride. The method is the most general among those reported to date as it applies to both acyclic ketones and aldehydes. Only moderate kinetic regioselectivity in favour of alk-1-yne achieved from methyl n-alkyl ketone represents a limitation of the method. In all the other instances, individual acetylenic products were obtained. Georg Thieme Verlag Stuttgart.
Lyapkalo, Ilya M.,Vogel, Michael A. K.,Boltukhina, Ekaterina V.,Vav?ík, Ji?í
scheme or table
p. 558 - 561
(2009/07/09)

Hybrid angiogenesis inhibitors: Synthesis and biological evaluation of bifunctional compounds based on 1-deoxynojirimycin and aryl-1,2,3-triazoles
Synthesis of hybrids of 1-deoxynojirimycin (DNJ) and 5-aryl-1,2,3-triazole as potential bifunctional inhibitors of angiogenesis is described. The DNJ component inhibits the biosynthesis of cell surface oligosaccharides necessary for angiogenesis, whereas the aryl-1,2,3-triazole inhibits methionine aminopeptidase II, a target in angiogenesis therapy. One bifunctional compound was a more potent inhibitor of angiogenesis in vitro than DNJ alone or the 5-aryl-1,2,3-triazole alone.
Zhou, Ying,Zhao, Yunxue,O' Boyle, Kathy M.,Murphy, Paul V.
p. 954 - 958
(2008/09/20)

Block modification of rod-shaped π conjugated carbon frameworks with donor and acceptor groups toward highly fluorescent molecules: Synthesis and emission characteristics
To create organic molecules that are highly fluorescent at a longer wavelength region, we investigated the synthesis (using Pd-catalyzed cross-coupling) and photophysical properties (Φ f, λ em, τ , λ abs, and ε ) of the following π conjugated molecular rods consisting of p-phenyleneethynylene units modified by donor (OMe) and/or acceptor (CN) groups: (1) side-donor modification systems (SD systems), (2) side-acceptor modification systems (SA systems), and (3) systems consisting of a donor block and an acceptor block (BL systems). As a consequence, very high Φ f values (>0.95) were obtained for BL systems. Bathochromic shifts of λ em for the same π conjugation length were largest for BL systems. Thus we succeeded in creating highly efficient light emitters at a longer wavelength region by block modification (e.g., Φ f = 0.97, λ em = 464 nm for BL-9). Considerably intense solid emission (Φ f ～ 0.5) at a longer wavelength region (500- 560 nm) was also found for BL systems. It has been found that BL-6 and BL-8 exhibit interesting two photon absorption characteristics. This journal is The Royal Society of Chemistry.
Ochi, Takanori,Yamaguchi, Yoshihiro,Wakamiya, Tateaki,Matsubara, Yoshio,Yoshida, Zen-Ichi
supporting information; scheme or table
p. 1222 - 1231
(2008/10/09)

Synthesis and photoluminescence studies of siloles with arylene ethynylene strands
Siloles attached to phenylene ethynylene strands were prepared successfully by Sonogashira coupling of 2,5-dibromosilole with ethyne-terminated phenylene ethynylenes. Elongation of the arylene ethynylene chain involving up to at least three aromatic rings
Ding, Changhua,Babu, Govindarajulu,Orita, Akihiro,Hirate, Takayoshi,Otera, Junzo
p. 2559 - 2563
(2008/02/13)

One-step synthesis of aromatic terminal alkynes from their corresponding ketones under microwave irradiation
One-step microwave-assisted synthesis of phenylacetylenes 2a-j from the corresponding ketones 1a-j in the presence of a new reagent, PCl 5 -pyridine, is described. The reaction is carried out under a simple operational and experimental procedure, avoiding the use of the complicated and harsh multistep reaction. Copyright Taylor & Francis Group, LLC.
Ghaffarzadeh, Mohammad,Bolourtchian, Mohammad,Fard, Zohreh,Halvagar, Mohammad,Mohsenzadeh, Farshid
p. 1973 - 1981
(2007/10/03)

INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
Compounds of formula (I) are hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors, and are useful in therapeutic and prophylactic treatment of persons infected with hepatitis C virus.
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(2010/02/07)

Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidase.
The synthesis of a novel series of 3-phenylprop-2-ynylamines as selective mammalian squalene epoxidase inhibitors is described. Structure activity relationship studies led to the discovery of compound 19, 1-[3-(3,5-dichlorophenyl)-prop-2-ynyl]-3- methylpiperidine hydrochloride with an IC50 of 2.8 +/- 0.6 microM against rat liver squalene epoxidase. Against 23 strains of fungal squalene epoxidase compound 19 was found to be inactive.
Musso, David L,Clarke, Morris J,Kelley, James L,Boswell, G Evan,Chen, Grace
p. 498 - 506
(2007/10/03)

Oxidation of aromatic compounds: VII oxidation of symmetrically substituted 1,3-diarylpropynones in the system CF3COOH-CH2Cl2-PbO2. New synthesis method of 1,1,2,2-tetraaroylethenes
Preparative oxidation of 1,3-diarypropynones ArC≡CCOAr in a system CF3COOH-CH2Cl2-PbO2 at 18-20°C within 1.5-25 h results in 1,1,2,2-tetraaroylethenes (ArCO)2C= C(COAr)2 in yields up to 75%. The most easily and efficiently the products form from the substrates where the aryl moiety conjugated with the triple bond contains electron-donating substituents p-MeO, p-Me, and p-t-Bu. On heating with hydrazine 1,1,2,2-tetrakis(4-methoxyphenylcarbonyl)ethene is converted into heterocyclic structures: pyridazine and 2,3,6,7-tetraazanaphthalene derivatives.
Vasil'ev,Rudenko,Grinenko
p. 1157 - 1162
(2007/10/03)

Derivatives of 2-arylcyclopropylamine: Synthesis and interactions with 5-HT1A receptors
A series of cis- and trans-derivatives of 2-aryl-N,N-dipropylcyclopropylamines and 1-(2-arylcyclopropyl)-N,N-dipropylmethylamines were synthesized and evaluated for affinity at the 5-HT1A receptor. The key step in the syntheses was a cyclopropanation of cis- and trans-3-arylpropenoic esters with diazomethane which proceeds with retention of the stereochemistry. cis-1-[2-(3-Methoxyphenyl)cyclopropyl]-N,N-dipropylmethylamine (32) had the highest 5-HT1A-receptor affinity (Ki= 58 nM) of the novel derivatives.
Appelberg, Ulf,Mohell, Nina,Hacksell, Uli
p. 415 - 420
(2007/10/03)

Synthesis and Electrochemical Properties of 4-Phenyl-1-buten-3-yne-1,1,2-tricarbonitriles and Tricyanoacrylates
The reaction of phenylacetylenes 4a-h copper(I) acetate (5) and TCNE (tetracyanoethylene) in THF/acetonitrile gave 4-phenyl-1-buten-3-yne-1,1,2-tricarbonitriles 6a-h. 4i did not react to give 6i.The phenylacetylenes 4b-i were prepared by a two-step synthesis starting from the corresponding phenyl halides 1b-i.The tricyanoacrylates 8 were synthesised from the corresponding cyanoacetates 7, TCNE and catalytic amounts of pyridine in THF. - Cyclovoltammetric investigations showed that the butenynes 6 and the tricyanoacrylates 8 are strong electron acceptors which can be easily reduced.The radical anions 6.- are unstable in acetonitrile and react irreversibly with 6 to give oligomeric anions 6.-n.Only 4-(2,4,6-trimethoxyphenyl)-1-buten-3-yne-1,1,2-tricarbonitrile (6h) is reduced to a radical anion 6h.- which associates with 6h in a reversible follow-up process to form a dimeric anion 6h2.-.By contrast, the tricyanoacrylates 8 can be reversibly reduced to their respective radical anions and dianions. - Keywords: Cyano compounds, conjugated / Phenylacetylenes / Radical anions / Electrochemistry
Dulog, Lothar,Koerner, Bernd,Heinze, Juergen,Yang, Jianjun
p. 1663 - 1672
(2007/10/02)

A Convergent Synthesis of Functionalized B-seco Taxane Skeletons
The sequential Sonogashira cross-coupling reactions with water soluble and anhydrous Pd(O) catalysts between vinylic iodo derivatives 6,8 and iodocyclohexenone 7 with trimethyl silyl acetylene are used to produce functionalized intermediates 11 and 18.Con
Montalbetti, Christian,Savignac, Monique,Bonnefis, Felicie,Genet, Jean Pierre
p. 5891 - 5894
(2007/10/02)

A convenient synthesis of 1-bromoolefins and acetylenes by a chain extension of aldehydes
Aldehydes are easily converted to 1-bromoolefins or terminal acetylenes by the use of Wittig reaction of bromomethylenetriphenylphosphorane which is prepared from bromomethyltriphenylphosphonium bromide with potassium tert-butoxide.
Matsumoto, Masakatsu,Kuroda, Keiko
p. 4021 - 4024
(2007/10/02)