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Redox-Neutral Cascade Trifluoromethylation of Dienes and Enynes using a Perylene Diimide (PDI) Organophotocatalyst 使用过二亚胺 (PDI) 有机光催化剂进行二烯烃和炔烃的氧化还原中性级联三氟甲基化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-05 DOI: 10.1002/adsc.202401040
Krishna Gopal Ghosh, Koustav Pal, Manasi Mallick, Debabrata Das, Devarajulu Sureshkumar
{"title":"Redox-Neutral Cascade Trifluoromethylation of Dienes and Enynes using a Perylene Diimide (PDI) Organophotocatalyst","authors":"Krishna Gopal Ghosh, Koustav Pal, Manasi Mallick, Debabrata Das, Devarajulu Sureshkumar","doi":"10.1002/adsc.202401040","DOIUrl":"https://doi.org/10.1002/adsc.202401040","url":null,"abstract":"The Perylene diimide (PDI) is an underexplored synthetic organic dye with significant potential in photoredox catalysis. We have developed a good chemo- and regioselective, atom-economical methodology for synthesizing trifluoroethylated saturated heterocyclic derivatives and trifluoroethyl-containing cyclobutane derivatives. This process involves the generation of trifluoromethyl radical from the Langlois (CF<sub>3</sub>SO<sub>2</sub>Na) reagent under photoredox conditions, which selectively reacts with the electron-rich terminal double/triple bonds in the diene/enyne framework. The resulting intermediate undergoes a cascade cyclization, yielding the desired compounds in a redox-neutral manner. Our methodology operates under very mild conditions, eliminating the need for transition metals and external oxidizing agents. It is broadly applicable across various substrates and is supported by comprehensive mechanistic insights from regular photophysical experiments.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"243 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142588986","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
Regio- and Diastereoselective One-pot Double Cascade Hybrid Formation/[3+3] Spirocyclization for the Synthesis of 3-Spiropiperidines Under Phase Transfer Conditions. 在相转移条件下，用于合成 3-螺哌啶类化合物的区域和非对映选择性单锅双级联杂化形成/[3+3] 螺环化。
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-05 DOI: 10.1002/adsc.202401230
Antonia Di Mola, Mohammad Sadeq Mousavi, Lorenzo Simeone, Giovanni Pierri, Antonio Massa
{"title":"Regio- and Diastereoselective One-pot Double Cascade Hybrid Formation/[3+3] Spirocyclization for the Synthesis of 3-Spiropiperidines Under Phase Transfer Conditions.","authors":"Antonia Di Mola, Mohammad Sadeq Mousavi, Lorenzo Simeone, Giovanni Pierri, Antonio Massa","doi":"10.1002/adsc.202401230","DOIUrl":"https://doi.org/10.1002/adsc.202401230","url":null,"abstract":"Herein, we report an efficient approach to synthesizing hybrid 3-spiropiperidines heterocycles that incorporate both 3-isochromanone and 3-isoindolinone units through a one-pot, double cascade reaction facilitated by an economical K₂CO₃/TBAB catalytic system. By examining the nucleophilicity of the lactone 3-isochromanone, we developed a cascade reaction pathway that first generates a bi-nucleophilic hybrid intermediate, which then undergoes [3+3] spirocyclization with α,β-unsaturated aldehydes. The regioselectivity of the spirocyclization strongly depends on the substitution pattern of lactam ring. The process exhibits high diastereoselectivity, even with the formation of three or four stereocenters, including two contiguous quaternary carbons. These sequential cascade reactions were successfully scaled up, and the subsequent reactivity was readily analyzed, enabling the transformation of existing functional groups into valuable new functionalities.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142588983","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
Anode material determined divergent 5-exo-dig cyclization of N-cyano-2-halobenzamides toward 3-iminoisoindolin-1-ones and 3-aminoisoindolin-1-ones 确定 N-氰基-2-卤代苯甲酰胺向 3-亚氨基异吲哚啉-1-酮和 3-氨基异吲哚啉-1-酮的 5-外-消化歧化环化的阳极材料
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-05 DOI: 10.1002/adsc.202401276
Xiao-Qing Xie, Zi-Qiong Li, Wei Zhou, Chaozhihui Cheng, Jiang Bai, Haixin Ding, Xian-Rong Song, Mu-Jia Luo, qiang xiao
{"title":"Anode material determined divergent 5-exo-dig cyclization of N-cyano-2-halobenzamides toward 3-iminoisoindolin-1-ones and 3-aminoisoindolin-1-ones","authors":"Xiao-Qing Xie, Zi-Qiong Li, Wei Zhou, Chaozhihui Cheng, Jiang Bai, Haixin Ding, Xian-Rong Song, Mu-Jia Luo, qiang xiao","doi":"10.1002/adsc.202401276","DOIUrl":"https://doi.org/10.1002/adsc.202401276","url":null,"abstract":"Herein, an electroreductive aryl radical enabled 5-exo-dig cyclization of N-cyano-2-halobenzamides is presented, providing a convenient route for the synthesis of a variety of 3-iminoisoindolin-1-ones in 30–75% yields. Simply by employing zinc plate instead of graphite rod anode, the products of the electrosynthesis are switched to diverse 3-aminoisoindolin-1-ones through aryl-radical-mediated 5-exo-dig cyclization and subsequent reductive hydrogenation. Furthermore, this anode material determined divergent 5-exo-dig cyclization features mild electrochemical conditions, excellent substrate scopes, and good functional group tolerance.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"33 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142589016","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 3‑Chloroindoles via Palladium-Catalyzed Chlorocyclization of Unmasked 2‑Alkynylanilines 通过钯催化未掩蔽的 2-炔基苯胺的氯环化合成 3-氯吲哚
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-04 DOI: 10.1002/adsc.202401296
Yongpeng Zheng, Jianxiao Li, Wanqing Wu, Chaorong Qi, Huanfeng Jiang
{"title":"Synthesis of 3‑Chloroindoles via Palladium-Catalyzed Chlorocyclization of Unmasked 2‑Alkynylanilines","authors":"Yongpeng Zheng, Jianxiao Li, Wanqing Wu, Chaorong Qi, Huanfeng Jiang","doi":"10.1002/adsc.202401296","DOIUrl":"https://doi.org/10.1002/adsc.202401296","url":null,"abstract":"Described herein is the discovery of a palladium-catalyzed chlorocylization strategy for the synthesis of 3‑chloroindoles tolerated with a wide range of functional groups in moderate to excellent yields. In this transformation, the solvent effect is so important that only THF presents the positive effect. Furthermore, the present method provides an essay access to the N-unprotected 3-chloroindoles. A mechanism study showed that 2-alkynlanilines were catalyzed by palladium to from corresponding indoles, followed by copper-mediated oxidation chlorination to deliver the 3-chloroindoles products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"87 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142579999","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
Visible-Light Enabled Synthesis of 1-Aryl-3-Sulfonylmethyl-1,2,4-Triazoles by Arylazo Sulfones 利用可见光通过芳基偶氮砜合成 1-芳基-3-磺酰基甲基-1,2,4-三唑
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-04 DOI: 10.1002/adsc.202401251
Luca Nicchio, Lorenzo Di Terlizzi, luc Neuville, Maurizio Fagnoni, Stefano Protti, Géraldine Masson
{"title":"Visible-Light Enabled Synthesis of 1-Aryl-3-Sulfonylmethyl-1,2,4-Triazoles by Arylazo Sulfones","authors":"Luca Nicchio, Lorenzo Di Terlizzi, luc Neuville, Maurizio Fagnoni, Stefano Protti, Géraldine Masson","doi":"10.1002/adsc.202401251","DOIUrl":"https://doi.org/10.1002/adsc.202401251","url":null,"abstract":"We present a novel and highly efficient method for synthesizing polyfunctionalized 1,2,4-triazoles. This approach leverages visible light and arylazo sulfones in combination with N-vinyl amides, in the environmentally friendly solvent ethyl acetate. Remarkably, the reaction proceeds without the need for (photo)catalysts, ensuring near-perfect atom economy and producing only water as a by-product. This method exhibits excellent functional group tolerance and can be scaled for both batch and continuous-flow processes.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"26 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142579876","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
Selective 1,2-Carboimination of Isothiocyanates to Access S-Substituted Isothioureas via Energy Transfer Catalysis 通过能量转移催化异硫氰酸酯的选择性 1,2-羧化反应获得 S-取代的异硫脲类化合物
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-04 DOI: 10.1002/adsc.202401233
Li-Ning Chen, Shu-Nuo Liang, Juan Luo, Dan-Na Chen, Zhi-Peng Ye, Peng-Ju Xia
{"title":"Selective 1,2-Carboimination of Isothiocyanates to Access S-Substituted Isothioureas via Energy Transfer Catalysis","authors":"Li-Ning Chen, Shu-Nuo Liang, Juan Luo, Dan-Na Chen, Zhi-Peng Ye, Peng-Ju Xia","doi":"10.1002/adsc.202401233","DOIUrl":"https://doi.org/10.1002/adsc.202401233","url":null,"abstract":"Herein, we introduce a novel method for the synthesis of S-substituted isothiourea compounds via the selective 1,2-carboimination between oxime esters as bifunctional reagents and the C=S bond of isothiocyanates under visible-light catalysis. This approach deviates from conventional methods by precisely modulating the substrate electronics to selectively functionalize the C=S bond of isothiocyanates over the C=N bond, eliminating the need for strong bases and high temperatures and bypassing the formation of thiourea intermediates. Consequently, this protocol enables the efficient one-step synthesis of S-alkyl isothioureas, with featuring mild reaction conditions, operational simplicity and broad substrate scope.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"67 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142580000","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
N-Oxide-Catalyzed Six-Membered Ring Bromo-etherification of ε-Alkenyl Alcohols N-氧化物催化的ε-烯醇六元环溴乙醚化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-03 DOI: 10.1002/adsc.202401209
Yuki Hoshino, Honoka Kasahara, Ryusei Marushima, Katsuhiko Moriyama
{"title":"N-Oxide-Catalyzed Six-Membered Ring Bromo-etherification of ε-Alkenyl Alcohols","authors":"Yuki Hoshino, Honoka Kasahara, Ryusei Marushima, Katsuhiko Moriyama","doi":"10.1002/adsc.202401209","DOIUrl":"https://doi.org/10.1002/adsc.202401209","url":null,"abstract":"A six-membered ring bromo-etherification of ε-alkenyl alcohols using <i>N</i>-oxide catalyst was developed to furnish 2-bromomethyl-6-substituted tetrahydropyrans with <i>cis</i>-selectivity and 3-bromomethyl isochromans in high yields. DFT calculations indicate that the NMO catalyst enhances the electrophilicity of the bromine atom on NBS via two hydrogen-bonding interactions after the formation of the NMO-NBS complex.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"48 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142574304","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
Iridium-Catalyzed Asymmetric Transfer Hydrogenation for Facile Access to Optically Active Dihydrodibenzo-Fused Azepines 铱催化不对称转移加氢反应，轻松获得具有光学活性的二氢二苯并融合氮杂环庚烷
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-03 DOI: 10.1002/adsc.202401200
Lijin Xu, Zhenni He, Ji Yang, Xiaohan Li, Wei Huang, Kai Liu, Qian Shi
{"title":"Iridium-Catalyzed Asymmetric Transfer Hydrogenation for Facile Access to Optically Active Dihydrodibenzo-Fused Azepines","authors":"Lijin Xu, Zhenni He, Ji Yang, Xiaohan Li, Wei Huang, Kai Liu, Qian Shi","doi":"10.1002/adsc.202401200","DOIUrl":"https://doi.org/10.1002/adsc.202401200","url":null,"abstract":"The asymmetric transfer hydrogenation of various dibenzo-fused azepines including 5H-dibenzo[b,e][1,4]diazepines, dibenzo[b,f][1,4]thiazepines and 11H-dibenzo[b,e]azepines using chiral iridium diamine catalysts and HCO2H/NEt3 as the hydrogen source has been accomplished. A rang of chiral 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines, 10,11-dihydrodibenzo[b,f][1,4]thiazepine and 6,11-dihydro-5H-dibenzo[b,e]azepines have been prepared in 82-94% yields with 82-99% ee. Diversely substituted substrates are suitable for this transformation, and a number of functional groups are tolerated. The enantiocontrol is achieved via judicious choice of catalyst, additive and hydrogen source. The synthetic potential of this reaction is explored through gram-scale reactions without loss of reactivity and optical purity and further transformations on products.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"54 12 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142574303","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
Direct Access to α,β-Unsaturated γ-Lactams via Palladium-Catalysed Carbonylation of Propargylic Ureas 通过钯催化丙炔基脲的羰基化直接获得α、β-不饱和γ-内酰胺
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-03 DOI: 10.1002/adsc.202401183
Debora Schiroli, Aleksandr Voronov, Francesco Pancrazzi, Nunzio Iraci, Salvatore Vincenzo Giofré, Beatrice Macchi, Valeria Stefanizzi, Raffaella Mancuso, Bartolo Gabriele, Paolo Pio Mazzeo, Luca Capaldo, Nicola Della Ca'
{"title":"Direct Access to α,β-Unsaturated γ-Lactams via Palladium-Catalysed Carbonylation of Propargylic Ureas","authors":"Debora Schiroli, Aleksandr Voronov, Francesco Pancrazzi, Nunzio Iraci, Salvatore Vincenzo Giofré, Beatrice Macchi, Valeria Stefanizzi, Raffaella Mancuso, Bartolo Gabriele, Paolo Pio Mazzeo, Luca Capaldo, Nicola Della Ca'","doi":"10.1002/adsc.202401183","DOIUrl":"https://doi.org/10.1002/adsc.202401183","url":null,"abstract":"Abstract. Additive carbonylations typically necessitate strong nucleophiles, such as alcohols or amines. In this study, we carbonylated a poorly nucleophilic urea, under oxidant-free conditions. Our straightforward carbonylative strategy enables access to versatile α,β-unsaturated γ-lactams featuring an aminocarbonyl fragment, utilizing readily available propargylic ureas as starting materials. The employment of the PdI2/KI catalytic system allowed complete regioselectivity (5-endo-dig), high functional group tolerance, broad substrate scope as well as operational simplicity (oxidant-free, organic ligand-free and base-free protocol). The synthetic utility of these γ-lactams is showcased through late-stage functionalizations, such as Giese reactions and peptide couplings.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"241 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142574305","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 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-01 DOI: 10.1002/adsc.202401179
Karthick Govindan, Chen Nian-Qi, 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, Chen Nian-Qi, Gokulakannan Venkatachalam, Tsz Fai Leung, Wei-Yu Lin","doi":"10.1002/adsc.202401179","DOIUrl":"https://doi.org/10.1002/adsc.202401179","url":null,"abstract":"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 N-(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 N-(3-acylamidopropyl)lactam derivatives with improved yields and shorter reaction time.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"9 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-01","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
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