Royal Society of Chemistry

Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes

Org. and Biomol. Chem. - 18 April, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00586H, CommunicationJinWu Zhao, Li Liu, ShiJian Xiang, Qiang Liu, HuoJi Chen
A TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes was developed.
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Identification of a Novel Class of Covalent Modifiers of Hemoglobin as Potential Antisickling Agents

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00367A, PaperAbdelsattar M Omar, Mona A Mahran, Mohini N Ghatge, Nadia Chowdhury, Faida H.A. Bamane, Moustafa E El-Araby, Osheiza Addulmalik, Martin Safo
Aromatic aldehydes and ethacrynic acid (ECA) exhibit antipolymerization properties that are beneficial for sickle cell disease therapy. Based on ECA pharmacophore and its atomic interaction with hemoglobin, we designed and...
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Rhodium-catalyzed denitrogenative thioacetalization of N-sulfonyl-1,2,3-triazoles with disulfides: an entry to diverse transformation of terminal alkynes

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00638D, CommunicationHao Zhang, Hui Wang, Haijun Yang, Hua Fu
An efficient and useful rhodium-catalyzed denitrogenative thioacetalization of N-sulfonyl-1,2,3-triazoles has been developed for the first time. The protocol uses readily available N-sulfonyl-1,2,3-triazoles and diaryl disulfides as the starting materials, the...
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Gold-catalyzed cascade C-H/C-H cross-coupling/cyclization/ alkynylation: An efficient access to 3-alkynylpyrroles

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00599J, CommunicationShuai Zhang, Yuanhong Ma, Jingbo Lan, Feijie Song, Jingsong You
An efficient approach to 3-alkynylpyrroles has been developed through the gold-catalyzed reaction of [small beta]-enamino derivatives with terminal alkynes, which features complete regiocontrol, relatively wide substrate scope, and high functional group...
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Palladium-Catalyzed Asymmetric Allylic Amination of Racemic Butadiene Monoxide with Isatin Derivatives

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00663E, PaperGen Li, Xiangqing Feng, HAIFENG DU
Isatins and their derivatives are important functional moities and building blocks in pharmaceutical and synthetic chemistry. Numerous enantioselective transformations at the C-3 carbonyl group have been well developed. However, the...
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A structure activity-relationship study of the bacterial signal molecule HHQ reveals swarming motility inhibition in Bacillus atrophaeus

Org. and Biomol. Chem. - 18 April, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00315F, PaperF. Jerry Reen, Rachel Shanahan, Rafael Cano, Fergal O'Gara, Gerard P. McGlacken
Swarming motility inhibition in Bacillus atrophaeus.
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Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones: One-pot reduction/aldol routes to 2,2-dichloro-3-hydroxy-1,3-diarylpropan-1-ones and related molecules

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00541H, PaperAli H. Essa, Reinner Ishaq Lerrick, Ece Ciftci, Ross Harrington, Paul G Waddell, William Clegg, Michael John Hall
2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles resulting in either reduction, reduction/aldol, reduction/Claisen condensation or reduction/aldol-Tishchenko products. In addition we...
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Tri- and tetra-substituted cyclen based lanthanide(III) ion complexes as ribonuclease mimics: A study into the effect of logKa, hydration and hydrophobicity on phosphodiester hydrolysis of the RNA-model 2-hydroxypropyl-4-nitrophenyl phosphate (HPNP)

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02384F, PaperAnn-Marie Fanning, Sally Elisabeth Plush, Thorfinnur Gunnlaugsson
A series of tetra-substituted 'pseudo' dipeptide ligands of cyclen (1,4,7,10,-tetraazacyclododecane) and a tri-substituted 3'-pyridine ligand of cyclen, and the corresponding lanthanide(III) complexes were synthesised and characterised as metallo-ribonuclease mimics. All...
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Direct Synthesis of a Geminal Zwitterionic Phosphonium / Hydridoborate System - Developing an Alternative Tool for Generating Frustrated Lewis Pair Hydrogen Activation Systems

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00634A, PaperGerald Kehr, G Erker, Jiangang Yu, Constantin Gabriel Daniliuc, Stefan Grimme, Christoph Bannwarth
A convenient way to the new class of geminal Mes2PH+/B(C6F5)2H- pairs is presented. It utilizes triflic acid addition to trans-Mes2PCH=CHB(C6F5)2 followed by triflate/hydride exchange. Thermally induced ring-closure gave a phosphonium/boratacyclopropane...
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The synthesis of new amphiphilic p-tert-butylthiacalix[4]arenes containing peptide fragments and their interaction with DNA

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00548E, PaperPavel Padnya, Elena Yushkova, Olga Mostovaya, Ildar Rizvanov, Ivan Stoikov
New water-soluble p-tert-butylthiacalix[4]arenes containing peptide and quaternary ammonium fragments in cone and 1,3-alternate conformations were synthesized and characterized. The interaction of the macrocycles with DNA was studied by UV-spectroscopy, DLS...
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Simultaneous Introduction of Trifluoromethyl and 6-Pentafluorosulfanyl Substituents using F5S-CC-CF3 as Dienophile

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00610D, CommunicationDieter Lentz, Blazej Duda
F5S-CC-CF3 can be easily prepared in high yields in two steps from 3,3,3-trifluoropropyne. It is a powerful, versatile dienophile in Diels-Alder reactions. Reactions at room temperature provide the corresponding products...
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Fluorine containing amino acids: Synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00650C, CommunicationDavid O'Hagan, Mohammed Salah Ayoup, David Bradford Cordes, Alexandra Slawin
A synthesis of two (S)-phenylalanine derivatives is described which have the all-cis, 2,3,5,6-tetrafluorocyclohexyl motif attached to the aromatic ring at the meta and para positions; the para substituted isomer is...
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Binaphthyl-1,2,3-Triazole Peptidomimetics with Activity Against Clostridium difficile and Other Pathogenic Bacteria

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00576K, PaperSteven M Wales, Katherine Hammer, Amy King, Andrew J Tague, Dena Lyras, Thomas V Riley, Paul Keller, Stephen G Pyne
Clostridium difficile (C. difficile) is a problematic Gram positive bacterial pathogen causing moderate to severe gastrointestinal infections. Based on a lead binaphthyl-tripeptide dicationic antimicrobial, novel mono-, di-and tri-peptidomimetic analogues targeting...
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77Se and 125Te NMR Spectroscopy on Selectivity Study of Organochalcogenanes with L-amino acids

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00373C, PaperMarcio Santos Silva, Leandro H. Andrade
The hypervalent selenium- and tellurium-containing compounds (halo-organoselenuranes and halo-organotelluranes) were treated with amino acids to evaluate their reactivity and chemoselectivity by 1H, 13C, 77Se and 125Te NMR Spectroscopy. The study...
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Synthetic studies toward the brasilinolides: controlled assembly of a protected C1-C38 polyol based on fragment union by complex aldol reactions

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00498E, PaperIan Paterson, Michael P. Housden, Christopher J. Cordier, Paul Matthew Burton, Friedrich A. Muhlthau, Olivier Loiseleur
The brasilinolides are an architecturally complex family of 32-membered macrolides, characterised by potent immunosuppressant and antifungal properties, which represent challenging synthetic targets. By adopting a highly convergent strategy, a range...
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Copper-Catalyzed Aerobic Oxidative Amination of C(sp3)-H bonds: Synthesis of Imidazo[1, 5-a]pyridines

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00381D, CommunicationAdimurthy Subbarayappa, Chandramohan Darapanenei, Sadu Nageswara Rao, Chitrakar Ravi
Copper-catalyzed synthesis of imidazo[1, 5-a]pyridine-1-carboxylates through oxidative amination of C(sp3)-H bonds under mild aerobic conditions with broad substrate scope is described. Use of naturally abundant air as a sole oxidant...
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Direct access to functionalized benzotropones, azepanes, and piperidines by reductive cross-coupling of [small alpha]-bromo enones with [small alpha]-bromo enamides

Org. and Biomol. Chem. - 18 April, 2015 - 05:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00517E, CommunicationTimothy K. Beng, Kayla Sincavage, Ann Wens V. Silaire, Amir Alwali, Daniel P. Bassler, Laura E. Spence, Oliver Beale
High-yielding syntheses of functionalized azepenes and piperidines, bearing an [small alpha]-benzotropone derivative, have been achieved through cobalt-catalysed reductive cross-coupling of [small alpha]-bromo enamides with [small alpha]-bromo enones.
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Copper(II)-Catalyzed Highly Regio- and Stereo-selective Hydrosilylation of Unactivated Internal Alkynes with Silylborate in Water

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00694E, CommunicationQing-Qing Xuan, Chuan-Li ren, Li Liu, Dong Wang, Chao-Jun Li
The highly regio- and stereoselective hydrosilylation of internal alkynes with silylborate catalyzed by Cu(OTf)2 with 1,10-phenanthroline as ligand in the presence of Cs2CO3 in water was developed. This protocol was...
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Divergent Synthesis of 4,6-Diarylated Pyridin-2(1H)-ones from Chalcones: Novel Access to 2,4,6-Triaryl Pyridines

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00545K, PaperRajni Khajuria, Prakash Kannaboina, Kamal Kapoor, Annah Gupta, Gourav Raina, Amanpreet Kaur, Love Karan Rana, Maninder Singh Hundal, Parthasarathi Das
A wide range of 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives were synthesized in good to excellent yields from 1,3-diarylated/heterylated-2-propen-1-ones (chalcones) in one pot under metal and base-free conditions. This domino reaction suggests a...
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A preorganized [small beta]-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides

Org. and Biomol. Chem. - 18 April, 2015 - 05:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00389J, CommunicationYosuke Demizu, Makoto Oba, Koyo Okitsu, Hiroko Yamashita, Takashi Misawa, Masakazu Tanaka, Masaaki Kurihara, Samuel H Gellman
A cyclic [small beta]-amino acid (APCGu) bearing a side-chain guanidinium group has been developed. The APCGu residue was incorporated into an [small alpha]/[small beta]-peptide based on the Tat(47-57) fragment, leading to an oligomer...
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