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Intramolcular Redox Reaction for the Synthesis of N-Aryl Pyrroles Catalyzed by Lewis Acids

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02009J, PaperHong-Jin Du, Le Zhen, Xiaoan Wen, Qing-Long Xu, Hongbin Sun
An efficient approach to N-aryl pyrroles via Lewis acid-mediated 1,5-hydride shift and isomerization of 2-(3-pyrroline-1-yl)arylaldehydes has been achieved in up to 89% yield. This methodology is applicable to the synthesis...
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Base-switched annuloselectivity in the reactions of ethyl malonyl chloride and imines

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01454E, PaperZhanhui Yang, Siqi Li, Zhong Zhang, Jiaxi Xu
The base-switched annuloselectivity, namely [2+2] and [2+2+2] selectivitiy, in the reactions of ethyl malonyl chloride and imines is successfully realized. In the presence of the weak nucleophilic base 2-chloropyridine, the...
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An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran by using alkoxybenzocyclobutenone as a reactive platform

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02012J, CommunicationToshiyuki Hamura, Kenta Asahina, Suguru Matsuoka, Ryosuke Nakayama
An efficient synthetic method of 1,3-bis(arylethynyl)isobenzofurans has been developed. Nucleophilic addition of alkynyllithium to benzocyclobutenone and subsequent oxidative ring cleavage of the four-membered ring gave keto-aldehyde, which, in turn, accepted...
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1-Trifluoromethylated isoquinolines via radical trifluoromethylation of isonitriles

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02145B, PaperBo Zhang, Armido STUDER
A simple and efficient approach to biologically important 1-trifluoromethylated isoquinolines starting with readily prepared beta-aryl-alpha-isocyano-acrylates and commercially available Togni reagent as CF3 radical precursor is described. These transformations occur in...
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An AIE active Y-shaped diimidazolylbenzene: aggregation and disaggregation for Cd2+ and Fe3+ sensing in aqueous solution

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01635A, CommunicationChengming Li, Chao Gao, Jingbo Lan, Jingsong You, Ge Gao
A simple Y-shaped dimb with AIE property was designed and synthesized. It showed selective fluorescence turn-on toward Cd2+ ion in MeCN/water (2:8, v/v) through aggregation, and also selective fluorescence turn-off...
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Conformational equilibria in selected A-type trimeric procyanidins

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02086C, PaperMarta Katarzyna Dudek (Jamroz), Slawomir Kazmierski, Kamil Stefaniak, Vitold B. Glinski, Jan A. Glinski
A-type procyanidin trimers: cinnamtannin B-1, cinnamtannin D-1, lindetannin, and aesculitannin B, were studied in terms of their conformation and interaction with four solvents: methanol, acetone, DMSO and pyridine. The experiments...
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Selective Oxygenation of Alkynes: A Direct Approach to Diketones and Vinyl Acetate

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01404A, PaperXiao-Feng Xia, Zhen Gu, Wentao Liu, Ningning Wang, Haijun Wang, yong-mei Xia, Haiyan Gao, Xiang Liu
Arylalkynes can convert into [small alpha]-diketones by the use of copper catalyst, and also transform into vinyl acetates under metal-free conditions both in the presence of PhI(OAc)2 as oxidant at room...
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Biosynthesis of 8-hydroxyquinoline-2-carboxylic acid, an iron chelator from the gut of the lepidopteran Spodoptera littoralis

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01857E, PaperJelena Pesek, Jiri Svoboda, Martina Sattler, Stefan Bartram, Wilhelm Boland
In the regurgitate (foregut content) of Spodoptera larvae we found high concentrations (0.5 - 5 mM) of 8-hydroxyquinoline-2-carboxylic acid (8-HQA). In a survey of different lepidopteran species, this compound was...
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Remote conformational control of a molecular switch via methylation and deprotonation

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01991A, PaperPeter C. Knipe, Ian M. Jones, Sam Thompson, Andrew D. Hamilton
Methylation and deprotonation at remote sites of a diphenylacetylene-based molecular switch exert global conformational changes through subtle tuning of a hydrogen-bonding network.
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Magnetic resonance and optical imaging probes for NMDA receptors on the cell surface of neurons: synthesis and evaluation in cellulo

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01848F, PaperNeil Sim, Robert Pal, David Parker, Joern Engelmann, Anurag Mishra, Sven Gottschalk
A second generation of N-methyl-D-aspartate (NMDA) receptor-targeted MRI contrast agents has been synthesised, based on bicyclic NMDA receptor antagonists and show selective and reversible cell-surface binding.
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Synthesis of nitriles via palladium-catalyzed water shuffling from amides to acetonitrile

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01825G, CommunicationWandi Zhang, Christopher W. Haskins, Yang Yang, Mingji Dai
Palladium-catalyzed synthesis of nitriles from amides has been described.
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Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01786B, CommunicationJieXiang Yin, Theresa Mekelburg, Christopher Hyland
The palladium(II)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (E)-allylsulfonamides. This stereoselectivity is complimentary to existing methods that typically proceed via an SN2[prime or minute] mechanism to yield (Z)-allylic systems.
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Total syntheses of cis-cyclopropane fatty acids: dihydromalvalic acid, dihydrosterculic acid, lactobacillic acid, and 9,10-methylenehexadecanoic acid

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01863J, PaperSayali Shah, Jonathan M. White, Spencer J. Williams
A systematic approach to the synthesis of enantiomeric pairs of the four title cis-cyclopropane fatty acids is reported.
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Highly regioselective synthesis of 3-alkenyl-oxindole ring-fused 3,3[prime or minute]-disubstituted oxindoles via direct gamma-substitution of Morita-Baylis-Hillman carbonates of isatins with 3-substituted oxindoles

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01523A, PaperTing-Ting Feng, Xuan Huang, Xiong-Li Liu, De-Hong Jing, Xiong-Wei Liu, Feng-Ming Guo, Ying Zhou, Wei-Cheng Yuan
The synthesis and antitumor activity evaluation of 3-alkenyl-oxindole ring-fused 3,3[prime or minute]-disubstituted oxindoles.
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Thiol-assisted one-pot synthesis of peptide/protein C-terminal thioacids from peptide/protein hydrazides at neutral conditions

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01885K, PaperChenchen Chen, Yichao Huang, Ling Xu, Yong Zheng, Huajian Xu, Qingxiang Guo, Changlin Tian, Yiming Li, Jing Shi
An efficient thiol-assisted one-pot synthesis of peptide/protein C-terminal thioacids was achieved by using peptide/protein hydrazides precursors at neutral pH and room temperature (about 20 [degree]C).
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A review of methods to synthesise 4[prime or minute]-substituted nucleosides

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01449A, Review ArticleMark Betson, Nigel Allanson, Philip Wainwright
Modified nucleosides have received a great deal of attention from the scientific community, either for use as therapeutic agents, diagnostic tools, or as molecular probes.
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Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB02056A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Alexander S. Henderson, John F. Bower, M. Carmen Galan
Versatile syntheses of C2-linked and C2-symmetric carbohydrate-based NHC[middle dot]HCls from functionalised amino-carbohydrate derivatives are reported. The corresponding Rh complexes were evaluated in asymmetric hydrosilylation of ketones.
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Rhodium(III)-catalyzed C-H alkynylation of azomethine ylides under mild conditions

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01596G, CommunicationXueyun Zhang, Zisong Qi, Jian Gao, Xingwei Li
Rh(III) complexes catalyzed the ortho C-H alkynylation of azomethine imine, which acts as a masked aldehyde group.
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RhIII-catalyzed dual directing group assisted sterically hindered C-H bond activation: a unique route to meta and ortho substituted benzofurans

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01876A, CommunicationChien-Hung Yeh, Wei-Chen Chen, Parthasarathy Gandeepan, Ya-Chun Hong, Cheng-Hung Shih, Chien-Hong Cheng
A new strategy for the synthesis of highly substituted benzofurans from meta-substituted hydroxybenzenes and alkynes via a rhodium(III)-catalyzed activation of a sterically hindered C-H bond is demonstrated.
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Asymmetric organocatalytic SOMO reactions of enol silanes and silyl ketene (thio)acetals

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01385A, PaperPavol Tisovsky, Maria Meciarova, Radovan Sebesta
The reactivity of aldehydes and ketones in asymmetric organo-SOMO reactions with enol silanes was explored. The best results were obtained with 3-phenylpropanal and tetralone-derived silyl enol ether and silyl ketene thioacetal.
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