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Thianthrenation-Enabled α-Arylation of Carbonyl Compounds with Arenes.

Xiao-Xue Nie, Yu-Hao Huang, Peng Wang,

The Pd-catalyzed α-arylation of carbonyl compounds with simple arenes enabled by site-selective thianthrenation has been demonstrated. This one-pot process using thianthrenium salts as the traceless arylating reagents features mild conditions and a broad substrate scope. In addition, this protocol could also tolerate the heterocyclic carbonyl compounds and complex bioactive molecules, ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Strategic Construction of Ethene-Bridged BODIPY Arrays with Absorption Bands Reaching the Near-Infrared II Region.

Qinghua Wu, Zhengxin Kang, Qingbao Gong, Xing Guo, Hua Wang, Dandan Wang, Lijuan Jiao, Erhong Hao,

An efficient strategy for the controllable synthesis of BODIPY arrays based on the Stille cross-coupling reaction has been developed, from which a family of well-defined ethene-bridged BODIPY arrays from dimer to hexamer was synthesized. These arrays showed strong absorptions reaching the near-infrared II (NIR II, 1000-1700 nm) region with maxima ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Metal-Free Radical-Mediated C(sp3)-H Heteroarylation of Alkanes.

Xin Shao, Xinxin Wu, Shuo Wu, Chen Zhu,

Herein we disclose a metal-free, N/O-centered radical-promoted Minisci reaction, in which the coupling of various heteroarenes with simple alkanes proceeds under mild conditions. The reaction conditions are neutral; no extra acid is added to preactivate N-heteroarenes in the Minisci reaction. The N-/O-centered radicals are generated directly from amide (TsNHMe) or ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Synthesis of 4-Alkylated Isocoumarins via Pd-Catalyzed α-Arylation Reaction.

Shane Plunkett, Lindsey G DeRatt, Scott D Kuduk, Jaume Balsells,

A convergent method for the rapid preparation of substituted isocoumarins is reported. The transformation takes advantage of a spontaneous intramolecular cyclization that follows the Pd-catalyzed α-arylation of aldehydes with 2-halobenzoic esters. The reaction uses an air-stable, single-component palladium catalyst and provides access to 4-alkylated isocoumarins in one step from commercial ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Effect of Twisting on the Capture and Release of Singlet Oxygen by Tethered Twisted Acenes.

Anjan Bedi, Amit Manor Armon, Ori Gidron,

The use of polyaromatic hydrocarbons to capture and release singlet oxygen is of considerable importance in materials chemistry, synthesis, and photodynamic therapy. Here we studied the ability of a series of tethered twistacenes, possessing different degrees of backbone twist, to capture and release singlet oxygen via the reversible Diels-Alder reaction. ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Copper-Catalyzed Anti-Markovnikov Hydrosilylation of Terminal Alkynes.

Zi-Lu Wang, Feng-Lian Zhang, Jian-Lin Xu, Cui-Cui Shan, Meng Zhao, Yun-He Xu,

A copper-catalyzed anti-Markovnikov hydrosilylation of alkynes with PhSiH3 was reported. This reaction represents a notable and efficient example on copper-catalyzed hydrosilylatioin of alkynes, which shows excellent recognition between the terminal and internal triple bonds. Various (hetero)aromatic and aliphatic substituted terminal alkynes underwent this reaction to afford the (E)-vinylsilanes in high ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN3 Pincer Catalyst.

Natalie Hofmann, Leonard Homberg, Kai C Hultzsch,

A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Oxetane Intermediate during a Direct Aldol Reaction: Stereoselective [5 + 1] Annulation Affording Tetralines.

Takeshi Kuri, Yoshihiko Mizukami, Mio Shimogaki, Morifumi Fujita,

An oxetane intermediate during a direct aldol reaction was trapped with an internal aryl group to yield trans-tetraline products. The contribution of the oxetane intermediate was confirmed by 18O-isotope labeling experiments. ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Selective Synthesis of Phenanthrenes and Dihydrophenanthrenes via Gold-Catalyzed Cycloisomerization of Biphenyl Embedded Trienynes.

Ana Milián, Patricia García-García, Adrián Pérez-Redondo, Roberto Sanz, Juan J Vaquero, Manuel A Fernández-Rodríguez,

Readily available o'-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evolution of the gold intermediate and plays a key role in the ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Chiral Calcium Phosphate Catalyzed Enantioselective Amination of 3-Aryl-2-benzofuranones.

Ruihan Liu, Suvratha Krishnamurthy, Zhenwei Wu, K S Satyanarayana Tummalapalli, Jon C Antilla,

A 4-tert-butyl-phenyl substituted (R)-[H8]-BINOL chiral calcium phosphate catalyzed enantioselective amination of 3-aryl-2-benzofuranones with dibenzyl azodicarboxylate is described. The catalyst loading of the reaction is 1 mol %. This transformation is facile and has a high degree atom economy, which gave products with good yields and high enantioselectivities (79% to 99%). ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Chalcogenide-Catalyzed Intermolecular Electrophilic Thio- and Halofunctionalization of gem-Difluoroalkenes: Construction of Diverse Difluoroalkyl Sulfides and Halides.

Quanbin Jiang, Yaoyu Liang, Yuanyuan Zhang, Xiaodan Zhao,

Thio- and halodifluoromethylated compounds are an important class of compounds in medicinal chemistry and organic synthesis. Herein, we report a facile method for the construction of these compounds via chalcogenide-catalyzed intermolecular electrophilic thio- and halofunctionalization of gem-difluoroalkenes. Simple treatment of gem-difluoroalkenes with electrophilic sulfur/halogen reagents and various O- or N-nucleophiles ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Vinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation.

Yu-Lan Zhang, Lei Yang, Jie Wu, Chunyin Zhu, Peng Wang,

Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl radical precursor, metal-free decarboxylative alkenylation with vinyl sulfonium salts was realized using eosin Y ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives.

Jian-Fei Wang, Xin Meng, Chao-Huan Zhang, Chuan-Ming Yu, Bin Mao,

Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of β-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized β-alkynyl-β-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Catalytic Direct Construction of Cyano-tetrazoles.

Ming-Yang Xiao, Meng-Meng Zheng, Xing Peng, Xiao-Song Xue, Fa-Guang Zhang, Jun-An Ma,

Cyano-tetrazole is the first reported compound that bears four nitrogen atoms in a single five-membered ring. This unique molecular scaffold has long been ignored after its discovery in 1885, mainly attributed to the scarcity of available synthetic methods. Indeed, the most popular approach to tetrazoles (that is the cycloaddition reaction ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Imidazole-Selective Alkyne Hydroamination under Physiological Conditions.

Hyung-Joon Kang, Joon-Ho Lee, Dong-Hyun Kim, Cheon-Gyu Cho,

Imidazole-selective intermolecular hydroamination reaction has been discovered. This unprecedented additive-free addition reaction proceeds in an exclusively regioselective and stereoselective manner with high atom economy under extremely mild reaction conditions. ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones.

Di Meng, Yangxi Xie, Qiupeng Peng, Jian Wang,

The unprecedented enantioselective NHC-catalyzed [3 + 3] annulation of α-bromoenals with amidines via a dual C-N bond formation is described. The protocol allows a rapid preparation of 5,6-dihydropyrimidinones in acceptable yields with good enantioselectivities. ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Chemically Fueled Transient Geometry Changes in Diphenic Acids.

Isuru M Jayalath, Hehe Wang, Georgia Mantel, Lasith S Kariyawasam, C Scott Hartley,

Transient changes in molecular geometry are key to the function of many important biochemical systems. Here, we show that diphenic acids undergo out-of-equilibrium changes in dihedral angle when reacted with a carbodiimide chemical fuel. Treatment of appropriately functionalized diphenic acids with EDC (N-(3-(dimethylamino)propyl)-N'-ethylcarbodiimide hydrochloride) yields the corresponding diphenic anhydrides, reducing ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols.

Susana Estopiñá-Durán, Euan B Mclean, Liam J Donnelly, Bryony M Hockin, James E Taylor,

The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C-C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Divergent Synthesis of Trifluoromethyl Sulfoxides and β-SCF3 Carbonyl Compounds by Tandem Trifluoromethylthiolation/Rearrangement of Allylic and Propargylic Alcohols.

Deng Zhu, Tong-Mei Ding, Hui-Yun Luo, Hua Ke, Zhi-Min Chen,

A selenium-catalyzed trifluoromethylthiolation/[2,3]-sigmatropic rearrangement of tertiary allylic and propargylic alcohols which could provide straightforward and facile access to trifluoromethyl sulfoxides was developed. Various allylic and allenic trifluoromethyl sulfoxides were obtained with moderate to excellent yields. Meanwhile, a Lewis acid mediated trifluoromethylthiolation/1,2-rearrangement to synthesize β-SCF3 carbonyl compounds was also accomplished. These ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Catalytic Asymmetric Synthesis of Atropisomeric Nitrones: Versatile Intermediate for Axially Chiral Biaryls.

Wenjing Guo, Jian Gu, Zhenhua Gu,

A Cu-catalyzed asymmetric ring-opening reaction of five-membered diaryliodonium salts and oximes is introduced. The reactions undergo selective N-arylation of oximes and provide an efficient protocol for the synthesis of atropisomeric nitrones. The optically active nitrones, serving as versatile intermediates, were converted to diversely functionalized axially chiral aniline derivatives and N-heterocycles. ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Unified Total Synthesis of Pentacyclic Stemoamide-type Alkaloids.

Yasuki Soda, Yasukazu Sugiyama, Makoto Yoritate, Hayato Tajima, Kana Shibuya, Chisato Ogihara, Takeshi Oishi, Takaaki Sato, Noritaka Chida,

The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for a comprehensive biological profiling of these natural products. In this Letter, we report a unified synthesis of seven pentacyclic alkaloids and two unnatural derivatives. The keys to success are (1) the chemoselective assembly ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Oligo(5-amino-N-acylanthranilic acids): Amide Bond Formation without Coupling Reagent and Folding upon Binding Anions.

Ruikai Cao, Robert B Rossdeutcher, Xiangxiang Wu, Bing Gong,

Oligomers of 5-amino-N-acylanthranilic acid, previously unknown aromatic oligoamides that cannot be obtained with known amide coupling methods, are synthesized based on a new, highly efficient amide-bond formation strategy that takes advantage of the ring-opening of benzoxazinone derivatives. These oligoamides offer multiple backbone NH groups as H-bond donors which, in the ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity.

Renyu Guo, Sarah R Beattie, Damian J Krysan, M Kevin Brown,

A synthesis of the reported antifungal agent (+)-hippolide J is presented. The rapid assembly of the natural product was enabled through implementation of an enantioselective isomerization/[2 + 2]-cycloaddition sequence. Due to the simplicity of the route, >100 mg of the natural product were prepared in a single pass. Anitfungal assays ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Visible-Light-Mediated C-H Alkylation of Pyridine Derivatives.

Fatima Rammal, Di Gao, Sondes Boujnah, Annie Claude Gaumont, Aqeel A Hussein, Sami Lakhdar,

We report herein a visible-light-mediated C-H alkylation of pyridine derivatives that proceeds by simple combination of a large variety of N-alkoxypyridinium ions with alkanes in the presence of 2 mol % of fac-Ir(ppy)3 under blue illumination. The mild reaction conditions together with the high group functional tolerance make of this ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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Access to Chiral Rigid Hemicyanine Fluorophores from Tröger Bases and α-Imino Carbenes.

Nidal Saleh, Alessandro Bosmani, Céline Besnard, Thomas Bürgi, Denis Jacquemin, Jérôme Lacour,

Chiral hemicyanine fluorophores are afforded in three steps only from Tröger bases via α-imino carbene additions, an original aminal deprotection and Cu(II)-mediated oxidation. The stable benzodiazepinoindolium salts are readily isolated and present (chir)optical properties that can be fine-tuned by late-stage cross-coupling functionalization. The hemicyanine character of dyes was rationalized using ... Read more >>

Org. Lett. (Organic letters)
[2020, :]

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