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The Latest Insights into Multiply Selective Diels–Alder Reactions Using a Chiral‐Cavity‐Structured Lewis‐Acidic Boron Catalyst 使用手性-空腔-结构Lewis -酸性硼催化剂的多重选择性diel - alder反应的最新见解
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-04 DOI: 10.1002/adsc.202401560
Kai Matsui , Kohei Toh , Tatsuhiro Sakamoto , Manabu Hatano , Kazuaki Ishihara
{"title":"The Latest Insights into Multiply Selective Diels–Alder Reactions Using a Chiral‐Cavity‐Structured Lewis‐Acidic Boron Catalyst","authors":"Kai Matsui ,&nbsp;Kohei Toh ,&nbsp;Tatsuhiro Sakamoto ,&nbsp;Manabu Hatano ,&nbsp;Kazuaki Ishihara","doi":"10.1002/adsc.202401560","DOIUrl":"10.1002/adsc.202401560","url":null,"abstract":"<div><div>The latest insights into multiply selective Diels–Alder (DA) reactions is presented, where a chiral‐cavity‐structured Lewis‐acidic boron catalyst is employed. The catalyst ((<em>R</em>)‐<strong>1</strong>) is capable of recognizing both dienes and dienophiles, primarily due to the influence of the suitable steric factors of its cavity. By taking advantage of the structural and <em>exo</em>‐product‐inducing properties of (<em>R</em>)‐<strong>1</strong>, even in the presence of a mixture of inseparable dienes, the target products were successfully obtained in high yield with high enantioselectivity. As (<em>R</em>)‐<strong>1</strong> exhibited the capacity to differentiate between three‐dimensional isomeric transition‐state structures in DA reactions, this work contributes to the advancement of artificial enzyme‐like catalysis, which has so far remained elusive.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 5","pages":"Article e202401560"},"PeriodicalIF":4.4,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142992366","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
Batch vs Continuous‐Flow Method to Synthesize N‐(3‐Acylamidopropyl)Lactams Through N−C Bond Cleavage in Amides with Amidines 通过酰胺与脒的 N-C 键裂解合成 N-(3-酰基酰胺丙基)内酰胺的批次法与连续流动法比较
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-04 DOI: 10.1002/adsc.202401179
Karthick Govindan , Nian‐Qi Chen , Gokulakannan Venkatachalam , Tsz‐Fai Leung , Wei‐Yu Lin
{"title":"Batch vs Continuous‐Flow Method to Synthesize N‐(3‐Acylamidopropyl)Lactams Through N−C Bond Cleavage in Amides with Amidines","authors":"Karthick Govindan ,&nbsp;Nian‐Qi Chen ,&nbsp;Gokulakannan Venkatachalam ,&nbsp;Tsz‐Fai Leung ,&nbsp;Wei‐Yu Lin","doi":"10.1002/adsc.202401179","DOIUrl":"10.1002/adsc.202401179","url":null,"abstract":"<div><div>The selective N−C bond cleavage of amides to create value‐added products through a transition metal‐free approach has become a significant challenge. Here, we present a method to convert amides into <em>N</em>‐(3‐acylamidopropyl)lactams through sequential amide chemoselective N−C bond cleavage and amidine ring opening under mild conditions, applicable in batch and continuous flow processes. These methods utilize bench‐stable reagents and are operationally straightforward and mild, enabling synthesis on a gram scale with excellent functional group tolerance. Additionally, the synthetic feasibility of these reactions under flow conditions has proven to be highly efficient, providing <em>N</em>‐(3‐acylamidopropyl)lactam derivatives with improved yields and shorter reaction time.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 5","pages":"Article e202401179"},"PeriodicalIF":4.4,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142563218","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
Chemodivergent Phototransformations of Green Fluorescent Protein Related Chromophores: Wavelength‐Dependent Photodimerization and Spirocyclization 绿色荧光蛋白相关发色团的化学变化：波长依赖性光二聚化和螺环化
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-04 DOI: 10.1002/adsc.202401001
Victoria E. Opryshko , Dmitrii S. Ivanov , Anastasia A. Danshina , Svetlana A. Krasnova , Artur V. Eshtukov‐Shcheglov , Andrey A. Mikhaylov , Alexander Yu. Smirnov , Mikhail S. Baranov
{"title":"Chemodivergent Phototransformations of Green Fluorescent Protein Related Chromophores: Wavelength‐Dependent Photodimerization and Spirocyclization","authors":"Victoria E. Opryshko ,&nbsp;Dmitrii S. Ivanov ,&nbsp;Anastasia A. Danshina ,&nbsp;Svetlana A. Krasnova ,&nbsp;Artur V. Eshtukov‐Shcheglov ,&nbsp;Andrey A. Mikhaylov ,&nbsp;Alexander Yu. Smirnov ,&nbsp;Mikhail S. Baranov","doi":"10.1002/adsc.202401001","DOIUrl":"10.1002/adsc.202401001","url":null,"abstract":"<div><div>Benzylidene imidazolones with an <em>ortho‐sec‐</em>amino group undergo chemodivergent photochemical transformations, based on the wavelength of irradiation. Irradiation at 525 nm causes dimerization and the formation of cyclobutanes with two spiroatoms, related to dictazoles in 87–98% yield. In turn, irradiation at 365 nm provides access to spirocyclic indolines in 67–92% yield. Each of the processes proceeds with exclusive atom economy and chemoselectivity.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 5","pages":"Article e202401001"},"PeriodicalIF":4.4,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142599593","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-Catalyzed Radical Alkylation/Cyclization of Isocyanides with Organoboron Reagents for Diversified Synthesis of N-Heteroaromatics
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-03 DOI: 10.1002/adsc.202500031
Wanqing Wu, Shichao Yang, Xiangwen Tan, Dan Liu
{"title":"Photoredox-Catalyzed Radical Alkylation/Cyclization of Isocyanides with Organoboron Reagents for Diversified Synthesis of N-Heteroaromatics","authors":"Wanqing Wu, Shichao Yang, Xiangwen Tan, Dan Liu","doi":"10.1002/adsc.202500031","DOIUrl":"https://doi.org/10.1002/adsc.202500031","url":null,"abstract":"The utility of alkyl boronic acids as alkyl radical precursors in photoredox-catalyzed reactions has been limited due to their low reactivity. A photoredox-catalyzed radical alkylation/cyclization of functional arylisocyanides with alkyl boronic acids is reported herein. This strategy allows the formation of alkyl radicals from boronic acids containing primary, secondary, and tertiary alkyl groups, which are subsequently transformed into structurally diverse alkylated products, including quinoxalines, phenanthridines, benzothiazoles, benzoselenazoles and quinolines. This transformation features readily available radical precursors and a broad substrate scope. The reaction mechanism is investigated by fluorescence quenching, light on/off, and cyclic voltammograms (CV) experiments. The combination of alkyl boronic acids with DBU may lead to the formation of the alkyl radical via a single electron transfer (SET) process, while the arylisocyanides may undergo an energy transfer (EnT) process with photocatalyst under visible light to generate the carbon radical or act as a radical acceptor to react with the alkyl radical.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"101 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143538337","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
Lanthanide One-Dimensional Coordination Polymer Catalyzed [3+2] Annulation Reaction: Synthesis of N,N’-Bicyclic Pyrazolidine Scaffolds
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-03 DOI: 10.1002/adsc.202401300
Rajendran Arunachalam, Ramaraj Selvaraj, Govinda Rajulu G, Karthikeyan Soundararajan, Shekhar M. S, Akshatha K. P, Palani Subramanian, Saravanan Subramanian, Sandeep S
{"title":"Lanthanide One-Dimensional Coordination Polymer Catalyzed [3+2] Annulation Reaction: Synthesis of N,N’-Bicyclic Pyrazolidine Scaffolds","authors":"Rajendran Arunachalam, Ramaraj Selvaraj, Govinda Rajulu G, Karthikeyan Soundararajan, Shekhar M. S, Akshatha K. P, Palani Subramanian, Saravanan Subramanian, Sandeep S","doi":"10.1002/adsc.202401300","DOIUrl":"https://doi.org/10.1002/adsc.202401300","url":null,"abstract":"Self-assembly of the multidendate ligand (H2L) with lanthanide metal salts leads to the formation of one-dimensional coordination polymers (CP). The structural analysis of the molecule suggests the formation of CP with ladder-type arrangements of ligands with metal centers. The polymers CP-1 and CP-2 with europium and terbium were found to be anionic and coordinatively unsaturated with the existence of solvent molecules in the vacant sites. The CPs were found to be suitable catalysts for the regioselective annulation of aza-MBH adducts with N,N, cyclic azomethine imines that lead to the formation of N,N’-bicyclic pyrazolidine scaffolds via [3+2] cycloaddition. The protocol tolerates a wide substrate scope with different functionalities by producing the bicyclic scaffold with better yield and excellent diastereoselectivity. The X-ray and NMR analysis suggests the formation of cis diastereomer which is stabilized by N-H---O interaction. The synthetic utility of the pyrazolidine scaffolds is attempted for various functional group interconversions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"34 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143538334","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
Synthesis of Tetrahydroisoquinolin-4-ones via Rh(II)-Catalyzed One-Pot Reaction of Aldehyde-Tethered N-Sulfonyl-1,2,3-Triazoles with Indoles
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-03-03 DOI: 10.1002/adsc.202401584
Hui Meng, Zehua Wang, Zefeng Xu, Chuan-Ying Li
{"title":"Synthesis of Tetrahydroisoquinolin-4-ones via Rh(II)-Catalyzed One-Pot Reaction of Aldehyde-Tethered N-Sulfonyl-1,2,3-Triazoles with Indoles","authors":"Hui Meng, Zehua Wang, Zefeng Xu, Chuan-Ying Li","doi":"10.1002/adsc.202401584","DOIUrl":"https://doi.org/10.1002/adsc.202401584","url":null,"abstract":"A rhodium(II)-catalyzed transannulation reaction between aldehyde-tethered N-sulfonyl-1,2,3-triazoles and indoles was reported, which resulted in the formation of functionalized tetrahydroisoquinolin-4-ones. This reaction is notable for its broad substrate scope, including a variety of N-sulfonyl-1,2,3-triazoles and different indoles. The addition of a protonic acid is essential for improving the yield of the desired tetrahydroisoquinolin-4-one products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"17 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143538664","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
Diastereoselective Synthesis of Oxabicyclo[3.3.1]nonenes from Aldehydes and α-Pinene: Fe(III) Aggregate Catalysis 醛和α-蒎烯非对映选择性合成氧杂双环[3.3.1]壬烯：铁(III)聚集催化作用
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-28 DOI: 10.1002/adsc.202401329
Sophi R. Todtz, Soumik Das, Paul M. Zimmerman, James J. Devery
{"title":"Diastereoselective Synthesis of Oxabicyclo[3.3.1]nonenes from Aldehydes and α-Pinene: Fe(III) Aggregate Catalysis","authors":"Sophi R. Todtz, Soumik Das, Paul M. Zimmerman, James J. Devery","doi":"10.1002/adsc.202401329","DOIUrl":"https://doi.org/10.1002/adsc.202401329","url":null,"abstract":"A challenge for the acid-mediated formation of oxabicyclo[3.3.1]nonenes is side product formation. Presented herein is a Lewis acid-catalyzed method towards these structures from aldehydes and α-pinene, forming the endo diastereomer exclusively. We include a proposal for the stereochemical reassignment of previously reported exo diastereomers supported by density functional theory (DFT) calculations, 1H NMR, and X-ray crystallography. The reactive system includes a range of aldehyde substrates. Experimental observations along with quantum chemical simulations suggest that an Fe(III)-aldehyde aggregate functions as the active catalyst.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"11 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143518289","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
Heterogeneously Catalyzed Cascade Oxidative Coupling/Dearomative Spirocyclization of Diarylamines: Facile Access to Spiroacridines
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-28 DOI: 10.1002/adsc.202500107
Kenji Matsumoto, Naho Sato, Yoshinori Kobayashi, Kanako Date, Yasuko Okamoto, Touya Kariya, Tsukasa Hirokane, Masahiro Yoshida
{"title":"Heterogeneously Catalyzed Cascade Oxidative Coupling/Dearomative Spirocyclization of Diarylamines: Facile Access to Spiroacridines","authors":"Kenji Matsumoto, Naho Sato, Yoshinori Kobayashi, Kanako Date, Yasuko Okamoto, Touya Kariya, Tsukasa Hirokane, Masahiro Yoshida","doi":"10.1002/adsc.202500107","DOIUrl":"https://doi.org/10.1002/adsc.202500107","url":null,"abstract":"Spirocyclic compounds, particularly spirocyclohexadienones, are important in pharmaceuticals due to their biological activity. In this study, we develop a catalytic cascade oxidative spirocyclization of diarylamines for the rapid access to highly functionalized spirocyclohexadienones. Using commercially available recyclable heterogeneous metal catalysts, cascade process via oxidative coupling and dearomative spiroannulation proceeds efficiently under mild aerobic conditions, providing spirocyclohexadienones fused with an acridine skeleton in good-to-excellent yields. This method provides efficient and rapid access to nitrogen-containing fused spiro compounds in a highly atom-economical and environmentally friendly manner.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"36 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143518292","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
Photo-Induced Oxidative C-H Esterification of Quinoxalinones with Arylaldehydes under Mild Conditions
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-28 DOI: 10.1002/adsc.202500018
Kai Zheng, Zhaoyang Wang, Yacong Wang, Chao Chen, Chao Shen
{"title":"Photo-Induced Oxidative C-H Esterification of Quinoxalinones with Arylaldehydes under Mild Conditions","authors":"Kai Zheng, Zhaoyang Wang, Yacong Wang, Chao Chen, Chao Shen","doi":"10.1002/adsc.202500018","DOIUrl":"https://doi.org/10.1002/adsc.202500018","url":null,"abstract":"The first example for photo-induced oxidative C-H esterification of quinoxalinones with arylaldehydes under benign conditions has been reported. This method is distinguished by its capacity to accommodate a diverse array of quinoxalinones and arylaldehydes, culminating in the synthesis of the corresponding esters with moderate to good yields. The protocol is lauded for its environmental benignity, eschewing the need for hazardous transition metals and costly photocatalysts, and relies solely on hydrogen peroxide (H2O2) as the oxidant. Moreover, the scalability of the synthesis and the derivative transformations of the products have been demonstrated, underscoring its practical utility in organic synthesis.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"72 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143526511","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
Front Cover Picture: (Adv. Synth. Catal. 4/2025)
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-27 DOI: 10.1002/adsc.202580401
{"title":"Front Cover Picture: (Adv. Synth. Catal. 4/2025)","authors":"","doi":"10.1002/adsc.202580401","DOIUrl":"https://doi.org/10.1002/adsc.202580401","url":null,"abstract":"<p>As of 2025, Advanced Synthesis and Catalysis joins the \u0000Advanced Portfolio from Wiley. Led by the world-renowned journal Advanced Materials, the Advanced Portfolio is a family of globally respected, high-impact journals that disseminate the best science. With the inclusion of Advanced Synthesis and Catalysis, it is broadening its reach into the field of chemistry. Cover image provided courtesy of Liang Zhao and co-workers from Dalian University of Technology.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 4","pages":""},"PeriodicalIF":4.4,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202580401","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143497066","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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