Diastereoselective Access to anti- β-Hydroxy Sulfoxides from Chiral Epoxides and Prochiral Sulfenate Anions: Mechanistic Insights, Scope, and Limitation
Synlett DOI: 10.1055/a-2196-5592 Reported herein is a stereoselective route to anti-β-hydroxy sulfoxides through the reaction of epoxides with sulfenate anions. Extensive experimental/computational studies revealed the dual special roles of MgBr2·OEt2, serving to generate the bromohydrin alkoxide intermediate, which undergoes nucleophilic attack on the prochiral sulfenate in a diastereoselective manner. The present study has opened a general stereoselective synthetic route to anti-β-hydroxy sulfoxides. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents...
Source: Synlett - November 21, 2023 Category: Chemistry Authors: Zhang, Jian Betkekar, Vipul V. Suzuki, Keisuke Ohmori, Ken Tags: letter Source Type: research
Asymmetric Cu(I)-Catalyzed Conjugate Borylation of α,β-Unsaturated Acyl Silanes
We report the development of a Cu(I)-catalyzed conjugate borylation of α,β-unsaturated acyl silanes using bis(pinacoloto)diboron. Racemic borylations of β-aryl- and β-alkyl-substituted silyl enones were achieved using ligand-free conditions to access β-borylated acyl silanes in up to 97% yield. Josiphos enabled the synthesis of enantioenriched boronic esters in up to 58% yield and 94% ee. The racemic reaction was demonstrated on 5.0 mmol scale and isolation of the boronic esters was achieved using simple filtration and normal-phase chromatography. This work supplements known methods to access boronic esters from elect...
Source: Synlett - November 21, 2023 Category: Chemistry Authors: Palermo, Anthony F. Imbriaco, Bianca Chan, Samantha C. Doan, Brian A. Rousseaux, Sophie A. L. Tags: letter Source Type: research
Synthesis of Alkyl Aryl Ethers by O-Arylation of Alcohols with Diaryliodonium Salts: Scope, Limitations, and Mechanism
We describe the development of a C–O coupling reaction between aryl(2,4,6-trimethoxyphenyl)iodonium salts and aliphatic alcohols under weak base conditions. The scope of the reaction is presented, with 16 examples ranging in yield from moderate to high (54–96%). The limitations of the reaction are also presented. Mechanistic experiments reveal a complex network of reactions that include side reactions that generate arynes and oxidize the alcohol nucleophile. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - November 21, 2023 Category: Chemistry Authors: Gallagher, Rory T. Jha, Soocheta Metze, Bryan E. Stuart, David R. Tags: letter Source Type: research
Microwave-Assisted Functionalization of Single-Walled Carbon Nanotubes as a Platform for a Supported Iridium Catalyst
Synlett DOI: 10.1055/a-2187-9368 Single-walled carbon nanotubes (SWCNTs) were functionalized by treatment with imino esters through 1,3-dipolar cycloaddition activated by thermal 1,2-prototropy. The reaction was optimized and analyzed by using various heating methods. The functionalization afforded pyrrolidino-functionalized nanotubes that were characterized by using several techniques. The ester group was then transformed into the corresponding SWCNT–iridium carboxylate and, as a proof of concept, the product was tested as a catalyst in the hydrogen-transfer reaction of acetophenone to yield 1-phenylethanol. [...] Georg...
Source: Synlett - November 20, 2023 Category: Chemistry Authors: Rodr íguez-Flórez, Lesly V. Retamosa, Mar ía de Gracia Mart ínez-Sánchez, Beatriz Cazorla-Amor ós, Diego N ájera, Carmen Yus, Miguel Sansano, Jos é M. Tags: letter Source Type: research
Evaluation of a Bidentate ‘Clamp-Like’ Halogen-Bond Donor Motif Based on Iodonium(III) Moieties
Synlett DOI: 10.1055/a-2198-3914 A new motif for iodine(III)-based halogen-bond donors consisting of a 1,3-phenylene core and two cyclic five-membered diaryliodonium(III) wings was designed and its potential as a catalyst was evaluated. Its properties were analyzed in the solid state by X-ray crystallography and in solution by benchmark catalytic activation of a nitro-Michael addition between 5-methoxyindole and trans-β-nitrostyrene. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - November 20, 2023 Category: Chemistry Authors: Reinhard, Dominik L. Kutzinski, Dana Hatta, Masahito Engelage, Elric Huber, Stefan M. Tags: cluster Source Type: research
Polyconjugated Materials for Printed (Opto)Electronics: Introducing Sustainability
Conclusion [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - November 20, 2023 Category: Chemistry Authors: Sassi, Mauro Mattiello, Sara Fappani, Alice Beverina, Luca Tags: account Source Type: research
Efficient Protosilylation of Unsaturated Compounds with Silylboronates over a Heterogeneous Cu3N Nanocube Catalyst
Synlett DOI: 10.1055/a-2191-5906 Copper-catalyzed protosilylation of unsaturated compounds with silylboronates has attracted attention for the production of organosilanes; however, the use of organic ligands or bases is unavoidable. Herein, we report a heterogeneous catalytic system for the protosilylation of unsaturated compounds with silylboronates under mild and additive-free conditions over copper nitride nanocubes (Cu3N NCs). This method can be applied to various substrates (e.g., alkynes, alkenes, or imines) to afford the corresponding organosilicon compounds. The Cu3N NC catalyst can be easily recovered and reused s...
Source: Synlett - November 17, 2023 Category: Chemistry Authors: Xu, Hang Yamaguchi, Sho Mitsudome, Takato Mizugaki, Tomoo Tags: letter Source Type: research
Synthesis of 2-Aminopyridine-Modified Peptide Nucleic Acids
Synlett DOI: 10.1055/a-2191-5774 Triplex-forming peptide nucleic acids (PNAs) require chemical modifications for efficient sequence-specific recognition of DNA and RNA at physiological pH. Our research groups have developed 2-aminopyridine (M) as an effective mimic of protonated cytosine in C+•G-C triplets. M-modified PNAs have a high binding affinity and sequence specificity as well as promising biological properties for improving PNA applications. This communication reports the optimization of synthetic procedures that give PNA M monomer in seven steps, with minimal need for column chromatography and in good yields and...
Source: Synlett - November 17, 2023 Category: Chemistry Authors: Kumpina, Ilze Baskevics, Vladislavs Walby, Grant D. Tessier, Brandon R. Saei, Sara Farshineh Ryan, Christopher A. MacKay, James A. Katkevics, Martins Rozners, Eriks Tags: letter Source Type: research
Stereocontrolled Aldol-Like Reactions Involving Oxocarbenium Intermediates
Conclusions [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - November 17, 2023 Category: Chemistry Authors: Galeote, Oriol Kennington, Stuart C. D. Mellado-Hidalgo, Miguel Costa, Anna M. Romea, Pedro Urp í, Fèlix Tags: account Source Type: research
Nickel-Catalyzed Hydroalkynylation of 1,3-Dienes with Simple Alkynes
Synlett DOI: 10.1055/s-0043-1763605 A hydroalkynylation reaction of 1,3-dienes with simple alkynes, facilitated by an efficient nickel catalyst system with the 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (Xantphos) ligand, is presented. This reaction displays a broad substrate range for alkynes, encompassing both aryl alkynes and alkyl alkynes, thereby overcoming previous constraints in 1,3-diene hydroalkynylation. The method offers a convenient and direct means for obtaining allylic alkynes with high atom and step economy. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJour...
Source: Synlett - November 16, 2023 Category: Chemistry Authors: Yao, Bo-Ying Xiao, Wei-Guo Xiao, Li-Jun Zhou, Qi-Lin Tags: letter Source Type: research
Copper-Catalyzed Regiodivergent Borylation of Fluorinated Alkynes and Palladium-Catalyzed Regiospecific Suzuki –Miyaura Cross-Coupling
We report herein highly regio- and stereoselective syntheses of α,Z- and β,Z-trifluoromethylated alkenylboranes by copper-catalyzed borylation reactions. Further functionalizations by palladium-catalyzed Suzuki–Miyaura cross-couplings have been developed and, interestingly, a marked difference in reactivity between the α- and β-borylated isomers has been identified. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - November 16, 2023 Category: Chemistry Authors: Rummler, L énaic Sater, Mariam Abd El Blanchard, Nicolas Bizet, Vincent Tags: letter Source Type: research
Bismuth-Centered Radical Species: Access and Applications in Organic Synthesis
Conclusions [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - November 16, 2023 Category: Chemistry Authors: Mart ínez, Sebastián Lichtenberg, Crispin Tags: account Source Type: research
Synergistic Organoboron/Palladium Catalysis for Regioselective N-Allylation of 2-Pyridones, 4-Pyridones, and Related Ambident Heterocycles
Synlett DOI: 10.1055/s-0043-1763618 The use of a boronic acid co-catalyst along with a palladium complex enables efficient dehydrative couplings of allylic alcohols and tautomerizable heterocycles. The protocol has been applied to achieve N-allylations of 2-pyridones, 4-pyridones, 4-pyrimidinones, and their benzofused derivatives. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - November 15, 2023 Category: Chemistry Authors: Yatzoglou, Giorgos Zambri, Matthew T. Desai, Shrey P. Taylor, Mark S. Tags: letter Source Type: research
Purine-Based AIEgens with Different Morpholine Substitution Sites and Their Application in Lipophagy Imaging
Synlett DOI: 10.1055/a-2201-3612 Lysosomes are an important organelle involved in many physiological processes. However, enhancing the accurate localization of lysosomes by chemical modification is still a problem. Herein, the purine-based AIEgens with different morpholine substitution sites were constructed. The effects of modification sites on the absorption, fluorescence, pH, viscosity and bioimaging properties of the probes were systematically studied. The morpholine modification at the phenyl site could effectively enhance the fluorescence behavior and the lysosome specificity. The morpholine-modified AIEgens could ac...
Source: Synlett - November 15, 2023 Category: Chemistry Authors: Shi, Lei Yu, Ai-Wen Meng, Wei-Han Xie, Kun-Peng Li, Kun Tags: cluster Source Type: research
Synform issue 2023/12
Synlett 2023; 34: A194-A216 DOI: 10.1055/s-0040-1720616 Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents (Source: Synlett)
Source: Synlett - November 14, 2023 Category: Chemistry Authors: Zanda, Matteo Tags: Synform Source Type: research
