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Photocatalyst-, Base- and Additive-Free, Visible-Light Induced 1,3-Thiosulfonylation of Allylboronic Esters and Allylketones with Thiosulfonates
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-26 DOI: 10.1002/adsc.202500051
Xin Zheng, Tuanli Yao, Kaiping Wang, Guodong Zhang, shuilong zhang, Xiang Li
{"title":"Photocatalyst-, Base- and Additive-Free, Visible-Light Induced 1,3-Thiosulfonylation of Allylboronic Esters and Allylketones with Thiosulfonates","authors":"Xin Zheng, Tuanli Yao, Kaiping Wang, Guodong Zhang, shuilong zhang, Xiang Li","doi":"10.1002/adsc.202500051","DOIUrl":"https://doi.org/10.1002/adsc.202500051","url":null,"abstract":"Abstract. A practical and highly efficient radical 1,3-thiosulfonylation of allylboron esters and allylketones with thiosulfonates via 1,2-functional group migration is described, affording diverse 1,3-thiosulfonylated products in good yields. Notably, this method can be performed under photocatalyst-, base- and additive-free conditions, which features operational simplicity, high atom-economy, excellent functional group tolerance and versatile transformations of the products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"7 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143518337","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Selectivity Rules for the Dearomative (3+2) Annulation Reaction Between Substituted Indoles and Oxyallyl Cations
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-26 DOI: 10.1002/adsc.202401536
Dhiman Saha, Jimmy Wu
{"title":"Selectivity Rules for the Dearomative (3+2) Annulation Reaction Between Substituted Indoles and Oxyallyl Cations","authors":"Dhiman Saha, Jimmy Wu","doi":"10.1002/adsc.202401536","DOIUrl":"https://doi.org/10.1002/adsc.202401536","url":null,"abstract":"We report a collection of “selectivity rules” for the dearomative (3+2) annulation reaction between substituted indoles and oxyallyl cations. The application of these rules enables us to synthesize four different regioisomeric permutations of the annulation products in a stereoselective fashion. We demonstrated that these products could be further transformed into hexahydro- and tetrahydrocarbazoles by nucleophile-intercepted Beckmann fragmentation (NuBFr) and Beckmann fragmentation (BFr).","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"44 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143518299","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Double-sided control of product type preference in the visible-light initiated reaction of 1,3-dicarbonyl compounds with alkenes
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-25 DOI: 10.1002/adsc.202500009
Małgorzata Pałyga, Jan Rzepiela, Sebastian Baś
{"title":"Double-sided control of product type preference in the visible-light initiated reaction of 1,3-dicarbonyl compounds with alkenes","authors":"Małgorzata Pałyga, Jan Rzepiela, Sebastian Baś","doi":"10.1002/adsc.202500009","DOIUrl":"https://doi.org/10.1002/adsc.202500009","url":null,"abstract":"Abstract. The demonstrated light-initiated addition of radicals formed on an active methylene group to styrene derivatives exhibits a product selectivity influenced by the presence of a protic solvent. Under protic conditions, the predominant products are branched compounds with the alkene moiety attached to the methylene group. In the absence of a proton source, an alkene is incorporated between the carbonyl group and the methylene group, forming products known from the De Mayo reaction. The utility of the presented method was confirmed by a broad substrate range of alkenes and compounds bearing active methylene groups. A comprehensive mechanistic study revealed that both types of products can be formed via the radical pathway. This suggests a previously unreported mechanistic path as an alternative to the De Mayo reaction, which gives the same type of products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"32 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143495756","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Catalytic γ-Position-Selective Reactions of (2-Oxopropyl)phosphonates with Aldehydes to Afford γ,δ-Unsaturated β-Ketophosphonates
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-25 DOI: 10.1002/adsc.202401375
James Osborne, Fujie Tanaka
{"title":"Catalytic γ-Position-Selective Reactions of (2-Oxopropyl)phosphonates with Aldehydes to Afford γ,δ-Unsaturated β-Ketophosphonates","authors":"James Osborne, Fujie Tanaka","doi":"10.1002/adsc.202401375","DOIUrl":"https://doi.org/10.1002/adsc.202401375","url":null,"abstract":"Catalytic formal aldol condensation reactions between β-ketophosphonates and arylaldehydes, in which the C-C double bond formation occurs at the γ-position of the β-ketophosphonate, are reported. The reactions were performed in the presence of a catalyst system composed of <i>p</i>-anisidine and trifluoroacetic acid under mild conditions. Mechanistic investigations suggest that a Mannich reaction followed by elimination results in the formation of the γ,δ-unsaturated β-ketophosphonate. Although the β-ketophosphonate has an active methylene group, the bond formation occurred selectively at the γ-position of the β-ketophosphonate.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"51 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143495757","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
FeCl3-Catalyzed Photochemical Reductive Transamidation of Nitroarenes: A Sustainable Approach Using Sacrificial C–H Bonds
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-25 DOI: 10.1002/adsc.202401574
Karthik Rajan Rajamanickam, Minwoo Park, Kyungho Park, Sunwoo Lee
{"title":"FeCl3-Catalyzed Photochemical Reductive Transamidation of Nitroarenes: A Sustainable Approach Using Sacrificial C–H Bonds","authors":"Karthik Rajan Rajamanickam, Minwoo Park, Kyungho Park, Sunwoo Lee","doi":"10.1002/adsc.202401574","DOIUrl":"https://doi.org/10.1002/adsc.202401574","url":null,"abstract":"A sustainable photochemical reductive transamidation of nitroarenes catalyzed by FeCl3 under blue LED irradiation is reported. This method eliminates the need for pre-reduction steps or stoichiometric reducing agents by utilizing sacrificial C-H bonds from organic solvents. The reaction proceeds via FeCl3-catalyzed single-electron transfer (SET) and hydrogen atom transfer (HAT) cascades. A previously unreported intermediate formed between nitroarenes and N-methylpyrrolidone (NMP) is discovered, playing a crucial role in facilitating substitution with amides. The method exhibits broad functional group tolerance and achieves yields up to 82%, demonstrating compatibility with a wide range of nitroarenes and amides.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143495552","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Photoredox assisted net-neutral radical-polar crossover α-acylation of enol acetates with acyl chlorides: Access to 1,3-diketones
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-24 DOI: 10.1002/adsc.202500007
Rohit Kumar, Harsha Harsha, Nidhi Jain
{"title":"Photoredox assisted net-neutral radical-polar crossover α-acylation of enol acetates with acyl chlorides: Access to 1,3-diketones","authors":"Rohit Kumar, Harsha Harsha, Nidhi Jain","doi":"10.1002/adsc.202500007","DOIUrl":"https://doi.org/10.1002/adsc.202500007","url":null,"abstract":"We report a photoredox assisted α-acylation of enol acetates with acyl chlorides using catalytic amount of Ir(ppy)3. The reaction proceeds via net-redox neutral radical-polar crossover pathway and furnishes 1,3-diketones in moderate to high yields under mild conditions without an external oxidant. The application of this method is demonstrated in the synthesis of Avobenzone (main ingredient in sunscreens), one-pot synthesis of anti-bacterial 4H-1,4-benzothiazines and organic-laser dye boron difluoride hemicurcuminoid complex.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143486416","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Organocatalytic Remote Stereocontrolled (4+2) Annulation of 2‐(4H‐Benzo[d][1,3]oxazin‐4‐yl)acrylates with 4‐Methyleneisoxazol‐5(4H)‐ones
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-21 DOI: 10.1002/adsc.202401603
Yan Liu, Xuling Chen, Pengfei Li
{"title":"Organocatalytic Remote Stereocontrolled (4+2) Annulation of 2‐(4H‐Benzo[d][1,3]oxazin‐4‐yl)acrylates with 4‐Methyleneisoxazol‐5(4H)‐ones","authors":"Yan Liu, Xuling Chen, Pengfei Li","doi":"10.1002/adsc.202401603","DOIUrl":"https://doi.org/10.1002/adsc.202401603","url":null,"abstract":"Despite the formidable challenge of concurrently managing both the regiochemistry and stereochemistry of the process, organocatalytic remote stereocontrol has emerged as an appealing approach to establish stereocenters at specified locations distant from reactive functional groups. Herein, we achieved the first organocatalyzed remote stereocontrolled (4+2) annulation of 2‐(4H‐benzo[d][1,3]oxazin‐4‐yl)acrylates with 4‐methyleneisoxazol‐5(4H)‐ones. The nucleophilic attack of a suitable chiral amine to 2‐(4H‐benzo[d][1,3]oxazin‐4‐yl)acrylates generated the key amine‐dipole intermediate, followed by the enantioselective aza‐1,4‐addition of 4‐methyleneisoxazol‐5(4H)‐ones and intramolecular annulation cascade reaction to construct spiro[isoxazole‐4,3’‐quinolin]‐5‐one frameworks bearing continuous three stereocenters. More importantly, different from the well‐established reactions of MBH carbonates, this work successfully established a novel platform for the direct enantioselective synthesis of continuous three stereocenters, inclusive of an ε‐stereocenter.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"182 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462929","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Advances of chiral metal complexes as standalone photocatalyst for asymmetric organic transformations
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-21 DOI: 10.1002/adsc.202401543
Anjan Das, A. John David, Balaji Ramachandran
{"title":"Advances of chiral metal complexes as standalone photocatalyst for asymmetric organic transformations","authors":"Anjan Das, A. John David, Balaji Ramachandran","doi":"10.1002/adsc.202401543","DOIUrl":"https://doi.org/10.1002/adsc.202401543","url":null,"abstract":"Many enantiopure chiral organic molecules are very important unit for drug discovery. Ready access to a wide range of enantiopure organic compounds, attached with one or more chiral centres significantly enhance the quality and diversity of chemical libraries for screening of drug discovery. The ability to control the stereochemistry of many organic reactions remains an area of interest in organic synthesis to allow the development of novel, structurally diverse 3D molecules. Asymmetric catalysis has been extensively studied for controlling the stereochemistry in modern synthetic organic chemistry. Recently, the use of light as the energy source with a chiral photocatalysts for photocatalytic asymmetric organic reactions has drawn much attentions but limited in numbers. The short lifetime of excited chiral photocatalysts and very fast reactions make the stereocontrol difficult in many reactions. However, by making a chiral photoactive metal complex with a suitable metal and ligands, this problem could be solved. As these chiral metal complexes are stable under light irradiation, versatile, having easy tuneable properties, these can provide more chiral inductions in many asymmetric organic reactions. So, in this review, we have focused on the recent development on chiral metal complexes as the standalone chiral photocatalysts for asymmetric organic reactions. We hope this review will help to understand the scopes and limitations to the research community in the field of asymmetric synthesis.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462930","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Base-Mediated Sequential Annulation Reaction of β-Pyrrol-α,β-Unsaturated Compounds with Vinylsulfonium Salts: A New Approach to Polycyclic Pyrrolizine Derivatives
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-20 DOI: 10.1002/adsc.202500032
Yuming Li, Yan Gou, Shuanghui Wang, Yaqi Xuan, Lulu Fu, Zhi Fan
{"title":"Base-Mediated Sequential Annulation Reaction of β-Pyrrol-α,β-Unsaturated Compounds with Vinylsulfonium Salts: A New Approach to Polycyclic Pyrrolizine Derivatives","authors":"Yuming Li, Yan Gou, Shuanghui Wang, Yaqi Xuan, Lulu Fu, Zhi Fan","doi":"10.1002/adsc.202500032","DOIUrl":"https://doi.org/10.1002/adsc.202500032","url":null,"abstract":"In this paper, we reported a novel sequential reaction sequence consisting of two processes including domino [3+2]/[2+1] annulation and in situ Cloke-Wilson rearrangement reaction, which enabled synthesis of a series of structurally complex polycyclic pyrrolizine derivatives in 51-96% yields and excellent diastereoselectivities. The viability of the existing protocol was additionally illustrated by gram-scale synthesis and further modifications. In addution, some of these valuable ring-fused pyrrolizines displayed some extent of anticancer activity, demonstrating their potential application in the medicinal chemistry.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"45 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463038","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Harnessing Indole-Derived Hydrazones for Enantioselective Synthesis of Pyrroloindolones via NHC-Catalyzed Formal [3+2]-Cycloaddition
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-19 DOI: 10.1002/adsc.202500016
Justyna Kowalska, Adam Cieśliński, Jose Julian Aleman Lara, Łukasz Albrecht
{"title":"Harnessing Indole-Derived Hydrazones for Enantioselective Synthesis of Pyrroloindolones via NHC-Catalyzed Formal [3+2]-Cycloaddition","authors":"Justyna Kowalska, Adam Cieśliński, Jose Julian Aleman Lara, Łukasz Albrecht","doi":"10.1002/adsc.202500016","DOIUrl":"https://doi.org/10.1002/adsc.202500016","url":null,"abstract":"Pyrrolo[1,2-a]indole derivatives are widely present in bioactive alkaloids and pharmaceuticals, with pyrroloindolones, containing a γ-lactam fused to an indole scaffold, forming a significant class of heteroaromatic compounds due to their presence in numerous natural products and biologically active molecules. In this study, we explored the potential of indole-derived hydrazones as 1,2-dinucleophiles in the N-heterocyclic carbene (NHC)-catalyzed formal [3+2]-cycloaddition with α-bromo-α,β-unsaturated aldehydes. A broad substrate scope was investigated, revealing the versatility of the method with various aldehydes and hydrazones. Subsequent transformations of the cycloaddition products demonstrated the synthetic utility of the developed methodology, preserving the optical purity of the final products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"25 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462710","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
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