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Synthesis of cyclic carbonates from CO2 and epoxides by novel metal and halide-free chiral boron compounds

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-20 DOI: 10.1016/j.tet.2025.134485

Ahmet Kilic , Valerio D’Elia , Emine Aytar , Chalida Phungpanya , Fatma Aslanli

The production of organic cyclic carbonates as valuable chemicals was carried out using a green and sustainable catalytic strategy for the environmentally friendly metal and halide-free CO₂ fixation. A series of novel chiral boron compounds (B₁ and B_1a-1d with B₂ and B_2a-2d) was synthesized, systematically characterized and applied for the synthesis of cyclic carbonates via CO₂ insertion into epoxides under reasonably mild reaction conditions. The prepared chiral boron compounds were characterized by NMR (¹H, ¹³C, and ¹¹B), FT-IR, UV–Vis spectroscopy, LC-MS/MS spectrometry. The thus characterized chiral boron compounds were used as Lewis acids for the cycloaddition reaction of CO₂ to epoxides in the presence of halide-free 4-dimethylaminopyridine (DMAP) as a nucleophilic catalytic component. Importantly, the performance of the newly synthesized compounds was also compared to that of a series of commercially available boron compounds. Halide-free commercially available boron Lewis acids generally showed lower conversion and/or selectivity under the applied reaction conditions that the newly synthesized compounds. The most active chiral boron compounds, dioxaborinanes (B_1a) and (B_1d), were selective for cyclic carbonate production under atmospheric pressure and were also screened under mild CO₂ pressures to afford higher conversion without significantly affecting cyclic carbonate selectivity.

{"title":"Synthesis of cyclic carbonates from CO2 and epoxides by novel metal and halide-free chiral boron compounds","authors":"Ahmet Kilic , Valerio D’Elia , Emine Aytar , Chalida Phungpanya , Fatma Aslanli","doi":"10.1016/j.tet.2025.134485","DOIUrl":"10.1016/j.tet.2025.134485","url":null,"abstract":"<div><div>The production of organic cyclic carbonates as valuable chemicals was carried out using a green and sustainable catalytic strategy for the environmentally friendly metal and halide-free CO2 fixation. A series of novel chiral boron compounds (B1 and B1a-1d with B2 and B2a-2d) was synthesized, systematically characterized and applied for the synthesis of cyclic carbonates via CO2 insertion into epoxides under reasonably mild reaction conditions. The prepared chiral boron compounds were characterized by NMR (1H, 13C, and 11B), FT-IR, UV–Vis spectroscopy, LC-MS/MS spectrometry. The thus characterized chiral boron compounds were used as Lewis acids for the cycloaddition reaction of CO2 to epoxides in the presence of halide-free 4-dimethylaminopyridine (DMAP) as a nucleophilic catalytic component. Importantly, the performance of the newly synthesized compounds was also compared to that of a series of commercially available boron compounds. Halide-free commercially available boron Lewis acids generally showed lower conversion and/or selectivity under the applied reaction conditions that the newly synthesized compounds. The most active chiral boron compounds, dioxaborinanes (B1a) and (B1d), were selective for cyclic carbonate production under atmospheric pressure and were also screened under mild CO2 pressures to afford higher conversion without significantly affecting cyclic carbonate selectivity.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134485"},"PeriodicalIF":2.1,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342868","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

ppm level Pd catalytic Suzuki-Miyaura coupling reaction in water and its application in the synthesis of Bixafen

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-17 DOI: 10.1016/j.tet.2025.134464

Zhiyong Tan , Tingting Chen , Jiayi Shen , Wenjun Luo , Daohong Yu , Jinbin Zhu , Minjie Zhang , Weihong Zhong , Wei Guo

We have developed a Pd-catalyzed Suzuki-Miyaura cross-coupling reaction for synthesizing key scaffold of important fungicides in water. The Pd-loading was as low as 30 ppm after optimization of experiment conditions with high TON. Additionally, the green, cheap and convenient ethanolamine was found to be as a highly efficient ligand for this transformation. Different heteroarylboronic halides and arylboronic acids were all suitable for construction of biphenyl scaffolds up to 98 % yield. We successfully carried out gram-scale experiments in two-step synthesis of Bixafen, making it a promising and environmental-friendly approach for industrialization.

引用次数: 0

Spiro-heterocycles: Recent advances in biological applications and synthetic strategies

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-17 DOI: 10.1016/j.tet.2025.134468

Basavaraja D , Siddalingeshwar V. Doddamani , Athira C. S , Aiswarya Siby , Sreelakshmi V , Ancy A , Sasidhar B. Somappa

Spiro-heterocycles garner much fascination due to their unique conformational features and vast biological applications than simple heterocycles. The number of spirocyclic scaffolds forms an integral part of drugs and drug candidates of synthetic and natural origin. Apart from the medicinal aspects, their applications are outstretched in material sciences and nanosciences. Furthermore, they are versatile building blocks for synthesizing biologically useful and structurally complex motifs. The construction of spiro-heterocycles, especially 3-8-membered spiro-rings, has been attractive for synthetic and medicinal chemists in the past few decades. Therefore, we have highlighted the biological significance and several protocols, including metal and metal-free mediated construction of structurally diverse spiro-heterocycles and related motifs in this review endower.

引用次数: 0

Green and eco-compatible synthesis of quinoxaline molecules using chitosan as a biodegradable catalyst in aqueous hydrotropic medium

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-15 DOI: 10.1016/j.tet.2025.134456

Aboli C. Sapkal , Suraj R. Attar , Nilam S. Dhane , Nilesh T. Pandit , Santosh B. Kamble

The development of green and sustainable methodologies for organic synthesis is an imperative step toward reducing the environmental impact of chemical processes. In this study, we present an efficient and eco-compatible method for the synthesis of quinoxaline derivatives using chitosan, a biodegradable and renewable catalyst, in an aqueous hydrotropic medium. Chitosan, derived from natural sources, acts as an effective biocatalyst, facilitating the reaction under mild conditions without hazardous organic solvents or harsh reagents. The use of a hydrotropic medium, specifically sodium toluene-4-sulfonate (NaPTS), enhances the solubility of reactants, leading to increased reaction rates and yields. This green approach provides significant advantages, including operational simplicity, low toxicity, and reduced waste generation. Moreover, the process is conducted in water, further promoting the sustainability of the reaction. The quinoxaline products obtained were characterized using standard spectroscopic techniques, confirming their structural integrity and purity. This method not only offers a greener alternative to traditional synthesis approaches but also aligns with the principles of green chemistry, making it suitable for large-scale applications in pharmaceutical and fine chemical industries.

{"title":"Green and eco-compatible synthesis of quinoxaline molecules using chitosan as a biodegradable catalyst in aqueous hydrotropic medium","authors":"Aboli C. Sapkal , Suraj R. Attar , Nilam S. Dhane , Nilesh T. Pandit , Santosh B. Kamble","doi":"10.1016/j.tet.2025.134456","DOIUrl":"10.1016/j.tet.2025.134456","url":null,"abstract":"<div><div>The development of green and sustainable methodologies for organic synthesis is an imperative step toward reducing the environmental impact of chemical processes. In this study, we present an efficient and eco-compatible method for the synthesis of quinoxaline derivatives using chitosan, a biodegradable and renewable catalyst, in an aqueous hydrotropic medium. Chitosan, derived from natural sources, acts as an effective biocatalyst, facilitating the reaction under mild conditions without hazardous organic solvents or harsh reagents. The use of a hydrotropic medium, specifically sodium toluene-4-sulfonate (NaPTS), enhances the solubility of reactants, leading to increased reaction rates and yields. This green approach provides significant advantages, including operational simplicity, low toxicity, and reduced waste generation. Moreover, the process is conducted in water, further promoting the sustainability of the reaction. The quinoxaline products obtained were characterized using standard spectroscopic techniques, confirming their structural integrity and purity. This method not only offers a greener alternative to traditional synthesis approaches but also aligns with the principles of green chemistry, making it suitable for large-scale applications in pharmaceutical and fine chemical industries.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"173 ","pages":"Article 134456"},"PeriodicalIF":2.1,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143315916","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

One-pot multistep carboxylation–oxidation of cage compounds

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-13 DOI: 10.1016/j.tet.2025.134472

Elena A. Ivleva, Yulia E. Khatmullina, Mikhail Yu. Skomorokhov, Yuri N. Klimochkin

An efficient one-pot approach to the synthesis of substituted 3-hydroxyadamantane-1-carboxylic acids has been developed. The method is based on the sequential combination of carboxylation by the Koch-Haaf reaction and oxidation in the presence of HNO₃ in H₂SO₄ or H₂SO₄·SO₃ medium, which allows COOH and OH to be appended together into the adamantane skeleton in the same reaction vessel. Due to their diverse functionality, the obtained compounds can be used as building blocks for the synthesis of new adamantane compounds with a many field of applications.

引用次数: 0

Effect of monosubstitution on the stability of phenylnitrene: A density functional theory study

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-12 DOI: 10.1016/j.tet.2025.134469

Juan Carlos Posadas-Hurtado , Francisco Méndez , Marco Martín González-Chávez , María de los Ángeles Zermeño-Macías

The effect of the substituent on the stability of phenylnitrenes has impact in their application of the synthesis de aza compounds and novel materials. The energy gaps ΔE_1A1–3A2, ΔE_1A2–3A2 and ΔE_1A1–1A2 for the 3A2, 1A2 and 1A1 states of para-, meta- and ortho-monosubstituted phenylnitrene with a set of electron-withdrawing or electron-donating substituents in the benzene ring were calculated at the DFT (M062X and B3LYP) and MP2 levels of theory and showed that the stability was 3A2>1A2>1A1. The ΔE trends ΔE_1A1–3A2 > ΔE_1A2–3A2 > ΔE_1A1–1A2 and ΔE_1A1–3A2 > ΔE_1A1–1A2 > ΔE_1A2–3A2 obtained for the electron-donating and electron-withdrawing substituents, respectively, indicated that the difference of stability between 3A2, 1A2 and 1A1 decreases as the substituent changes from electron-withdrawing to electron-donating. Electron-withdrawing substituent on para-, meta- and ortho-monosubstituted phenylnitrene causes its closed-shell singlet 1A1 to become less stable than its open-shell singlet 1A2 compared to those of phenylnitrene. The sensitive of the para-monosubstituted phenylnitrene to the effect of the electron-donating and electron-withdrawing substituents follows the trend ΔE_1A1–1A2 > ΔE_1A1–3A2 > ΔE_1A2–3A2. Correlation analysis between the Hammett constant (σ) with the ΔE_1A1–3A2 and ΔE_1A2–3A2 reveals that substituents produce energy changes that are linearly additive, and the resonance effects are more important than inductive effects.

{"title":"Effect of monosubstitution on the stability of phenylnitrene: A density functional theory study","authors":"Juan Carlos Posadas-Hurtado , Francisco Méndez , Marco Martín González-Chávez , María de los Ángeles Zermeño-Macías","doi":"10.1016/j.tet.2025.134469","DOIUrl":"10.1016/j.tet.2025.134469","url":null,"abstract":"<div><div>The effect of the substituent on the stability of phenylnitrenes has impact in their application of the synthesis de aza compounds and novel materials. The energy gaps ΔE1A1–3A2, ΔE1A2–3A2 and ΔE1A1–1A2 for the 3A2, 1A2 and 1A1 states of para-, meta- and ortho-monosubstituted phenylnitrene with a set of electron-withdrawing or electron-donating substituents in the benzene ring were calculated at the DFT (M062X and B3LYP) and MP2 levels of theory and showed that the stability was 3A2>1A2>1A1. The ΔE trends ΔE1A1–3A2 > ΔE1A2–3A2 > ΔE1A1–1A2 and ΔE1A1–3A2 > ΔE1A1–1A2 > ΔE1A2–3A2 obtained for the electron-donating and electron-withdrawing substituents, respectively, indicated that the difference of stability between 3A2, 1A2 and 1A1 decreases as the substituent changes from electron-withdrawing to electron-donating. Electron-withdrawing substituent on para-, meta- and ortho-monosubstituted phenylnitrene causes its closed-shell singlet 1A1 to become less stable than its open-shell singlet 1A2 compared to those of phenylnitrene. The sensitive of the para-monosubstituted phenylnitrene to the effect of the electron-donating and electron-withdrawing substituents follows the trend ΔE1A1–1A2 > ΔE1A1–3A2 > ΔE1A2–3A2. Correlation analysis between the Hammett constant (σ) with the ΔE1A1–3A2 and ΔE1A2–3A2 reveals that substituents produce energy changes that are linearly additive, and the resonance effects are more important than inductive effects.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"173 ","pages":"Article 134469"},"PeriodicalIF":2.1,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143356341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-12 DOI: 10.1016/j.tet.2025.134467

Jiaqing Shao, Jiang Liu, Haibo Mei, Jianlin Han

Electrochemical reaction has been becoming a powerful tool in organic synthesis, which provides green and efficient strategies for the construction of heterocyclic scaffolds. In this review article, recent advances in the generation of sulfonyl radical-triggered cyclization of unsaturated C–C bonds under electrochemical conditions have been summarized. According to the different types of sulfonyl radical precursors, the electrochemical cyclization reactions with sulfinate salts, sulfonyl hydrazides, and fluoroalkyl sulfinates as coupling partners have been presented. The reaction conditions, substrate scope, mechanism, and synthetic application, are discussed for each reaction.

引用次数: 0

Novel homochiral 2-oxazolines camphor derived as asymmetric organocatalysts in the glycosidic bond formation

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-11 DOI: 10.1016/j.tet.2025.134460

Gabriela Huelgas , Mildred López , Mario Sánchez , Vladimir Carranza-Tellez , Angel Mendoza , Cecilia Anaya de Parrodi

This study presents the synthesis of novel homochiral 2-oxazolines 13 – 24 via intramolecular cyclization of chiral 2-hydroxy-3-thioureas 1 – 12. The intramolecular cyclization occurred by nucleophilic attack of the hydroxy group over the thiocarbonyl bond employing methyl iodide and lithium carbonate in moderate to good yields (40–81 % yield). The newly synthesized 2-oxazolines 13 – 24 were evaluated as asymmetric organocatalysts (15 mol% loading) in the glycosylation of 2,3,4,6-tetra-O-benzyl-d-glucopyranosyl trichloroacetamidate 26 as donor (1 equiv), and methyl alcohol as glycosyl acceptor (2 equiv), under solvent-free conditions, at room temperature, after 96 h. The best stereoselectivity was achieved with 2-oxazoline 16, affording 66 % yield and 1:29 α/β ratio. Computational studies were conducted using the B3LYP-D4/def2-TZVP method to model complexes involving three catalysts (13, 15, and 16), aiming to gain deeper insight into the mechanisms governing their performance and the observed yields. Our analysis revealed that steric effects and hydrogen bonding interactions are pivotal in controlling the stereoselectivity during glycosidic bond formation. These findings underscore the significance of 2-oxazolines as versatile chiral organocatalysts in organic chemistry.

{"title":"Novel homochiral 2-oxazolines camphor derived as asymmetric organocatalysts in the glycosidic bond formation","authors":"Gabriela Huelgas , Mildred López , Mario Sánchez , Vladimir Carranza-Tellez , Angel Mendoza , Cecilia Anaya de Parrodi","doi":"10.1016/j.tet.2025.134460","DOIUrl":"10.1016/j.tet.2025.134460","url":null,"abstract":"<div><div>This study presents the synthesis of novel homochiral 2-oxazolines 13 – 24 via intramolecular cyclization of chiral 2-hydroxy-3-thioureas 1 – 12. The intramolecular cyclization occurred by nucleophilic attack of the hydroxy group over the thiocarbonyl bond employing methyl iodide and lithium carbonate in moderate to good yields (40–81 % yield). The newly synthesized 2-oxazolines 13 – 24 were evaluated as asymmetric organocatalysts (15 mol% loading) in the glycosylation of 2,3,4,6-tetra-O-benzyl-d-glucopyranosyl trichloroacetamidate 26 as donor (1 equiv), and methyl alcohol as glycosyl acceptor (2 equiv), under solvent-free conditions, at room temperature, after 96 h. The best stereoselectivity was achieved with 2-oxazoline 16, affording 66 % yield and 1:29 α/β ratio. Computational studies were conducted using the B3LYP-D4/def2-TZVP method to model complexes involving three catalysts (13, 15, and 16), aiming to gain deeper insight into the mechanisms governing their performance and the observed yields. Our analysis revealed that steric effects and hydrogen bonding interactions are pivotal in controlling the stereoselectivity during glycosidic bond formation. These findings underscore the significance of 2-oxazolines as versatile chiral organocatalysts in organic chemistry.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"173 ","pages":"Article 134460"},"PeriodicalIF":2.1,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143356339","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Convergent total synthesis of 4a,6-epi- and 4a,6,9-epi-diplopyrone

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-11 DOI: 10.1016/j.tet.2025.134462

Beduru Srinivas , Ram Prasnna , Debendra K. Mohapatra

The asymmetric convergent total synthesis of 4a,6-epi- and 4a,6,9-epi-diplopyrone were achieved in 15 longest linear steps starting from 1,4-butyne-diol. The synthetic route features regioselective epoxide opening, Sharpless asymmetric epoxidation (SAE), ring-closing metathesis (RCM), and Still−Gennari (Z)-selective oleﬁnation reactions. The spectroscopic (¹H and ¹³C NMR) as well as the analytical data for compound 7b and 7c did not match with the data reported for the putative structure for diplopyrone.

引用次数: 0

4-Aminobenzotriazole directed palladium-catalyzed C–H acetoxylation and intramolecular amination reaction

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-01-11 DOI: 10.1016/j.tet.2025.134470

Zhuo Wang , Chengqian Li , Yupeng Fan , Jianliang Hu , Wangsheng Huang , Yuanming Li , Zhiguang Song

We present an approach for ortho C(sp²)-H acylation and intramolecular amination reactions, employing 4-amino-benzotriazole (ABTA) as a bidentate directing group. This method is facilitated by a palladium catalyst in combination with iodobenzene diacetate. Our approach efficiently yields acetoxylation and intramolecular amination products from a variety of acylamide substrates, including arylcarboxamides and arylacetamides.

引用次数: 0

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