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Copper(I)‐Catalyzed Proto/Carboboration of Enyne Boronates for the Synthesis of Densely Substituted Diene Diboronates 铜(I)催化的炔硼酸原/碳硼酸化反应用于合成高密度取代的二烯二硼酸盐
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-12 DOI: 10.1002/adsc.202401188
Suman Ghosh, Rajesh Chakrabortty, Shailendra Kumar, Venkataraman Ganesh
{"title":"Copper(I)‐Catalyzed Proto/Carboboration of Enyne Boronates for the Synthesis of Densely Substituted Diene Diboronates","authors":"Suman Ghosh, Rajesh Chakrabortty, Shailendra Kumar, Venkataraman Ganesh","doi":"10.1002/adsc.202401188","DOIUrl":"https://doi.org/10.1002/adsc.202401188","url":null,"abstract":"A copper‐catalyzed carbo‐/protoboration of boryl enynes is disclosed, providing access to an array of penta‐ and hexasubstituted diboryl dienes in a chemo‐, regio‐ and stereoselective manner. All six positions of the dienes can be manipulated using this methodology. The hexasubstituted diene boronates adopt a skew conformation. An iterative Suzuki coupling of the products provided highly conjugated trienes and tetraenes.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"156 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142599589","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
Stereoconvergent Access to Z‐Allylborons from E/Z‐Mixed 1,3‐Dienes via Cu‐Guanidine Catalysis 通过铜-胍催化从 E/Z-Mixed 1,3-Dienes 立体交叉获得 Z-烯丙基硼
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-12 DOI: 10.1002/adsc.202401322
Ai Zhang, Huangfeng Zhang, Tao Jin, Lin Ge, Xiaoyan Ma, Jinghua Tang, Jin-Yu Liu, Choon-Hong Tan, Richmond Lee, Yicen Ge
{"title":"Stereoconvergent Access to Z‐Allylborons from E/Z‐Mixed 1,3‐Dienes via Cu‐Guanidine Catalysis","authors":"Ai Zhang, Huangfeng Zhang, Tao Jin, Lin Ge, Xiaoyan Ma, Jinghua Tang, Jin-Yu Liu, Choon-Hong Tan, Richmond Lee, Yicen Ge","doi":"10.1002/adsc.202401322","DOIUrl":"https://doi.org/10.1002/adsc.202401322","url":null,"abstract":"Merging the stereoisomeric mixture of substrate into a single product through stereospecific transformation is a challenging but higher‐order synthetic strategy, which perfectly meets the demand of cost control in the precise chemical production. In this work, the stereoconvergent synthesis of Z‐allylic boronates was realized with protoborylation of E/Z‐mixed 1,3‐dienes catalyzed by a novel copper‐guanidine complex. The reaction could proceed smoothly under very mild conditions with good functional group tolerance, and convert diverse aryl‐substituted 1,3‐dienes into the desired Z‐1,4‐addition products with excellent chemo‐, regio‐, and stereoselectivities in minutes. Detailed mechanistic studies also helped to disclose the origin of stereoconvergency. Both E‐ and Z‐diene were found directly undergoing a rapid borylation without E/Z isomerization of C=C bond, followed by a convergent formation of the same thermodynamically stable allylcopper intermediate before the slow protonation step occurred.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"18 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142599590","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
Asymmetric Transfer Hydrogenation of 3‐Substituted 2H‐1,4‐Benzoxazines under Tethered Cp*Rh(III)‐Diamine Catalysis with Unexpected Reversal of Enantioselectivity 系链 Cp*Rh(III)- 二胺催化下 3-取代 2H-1,4-苯并噁嗪的不对称转移加氢反应与意想不到的对映选择性逆转
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-12 DOI: 10.1002/adsc.202401307
Lijin Xu, Xiaohan Li, Ji Yang, Zhenni He, Wei Huang, Jianbo Yang, Huanrong Li, Qian Shi
{"title":"Asymmetric Transfer Hydrogenation of 3‐Substituted 2H‐1,4‐Benzoxazines under Tethered Cp*Rh(III)‐Diamine Catalysis with Unexpected Reversal of Enantioselectivity","authors":"Lijin Xu, Xiaohan Li, Ji Yang, Zhenni He, Wei Huang, Jianbo Yang, Huanrong Li, Qian Shi","doi":"10.1002/adsc.202401307","DOIUrl":"https://doi.org/10.1002/adsc.202401307","url":null,"abstract":"The asymmetric transfer hydrogenation of 3‐substituted 2H‐1,4‐benzoxazines with an azeotropic mixture of HCO2H/NEt3 (5/2) using tethered Cp*Rh(III)‐diamine catalysis has been realized. This process allows access to a broad range of chiral 3,4‐dihydro‐2H‐1,4‐benzoxazines in high yields with up to 99% ee, and tolerates a variety of functional groups. The enantiocontrol is achieved by the judicious choice of catalyst and hydrogen source. This reaction proceeds with unexpected reversal of enantioselectivity, which is attributed to the acidic reaction conditions and the hydrogen bond between the N−H of the rhodium species and the O atom in the substrate.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142599591","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 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-12 DOI: 10.1002/adsc.202401001
Victoria Opryshko, Dmitrii Ivanov, Anastasia Danshina, Svetlana Krasnova, Artur Eshtukov-Shcheglov, Andrey Mikhaylov, Alexander Smirnov, Mikhail Baranov
{"title":"Chemodivergent Phototransformations of Green Fluorescent Protein Related Chromophores: Wavelength‐Dependent Photodimerization and Spirocyclization","authors":"Victoria Opryshko, Dmitrii Ivanov, Anastasia Danshina, Svetlana Krasnova, Artur Eshtukov-Shcheglov, Andrey Mikhaylov, Alexander Smirnov, Mikhail Baranov","doi":"10.1002/adsc.202401001","DOIUrl":"https://doi.org/10.1002/adsc.202401001","url":null,"abstract":"Benzylidene imidazolones with an ortho‐sec‐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% yields. In turn, irradiation at 365 nm provides access to spirocyclic indolines in 67‐92% yields. Each of the processes proceeds with exclusive atom economy and chemoselectivity.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-12","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
Gold(I)-Catalyzed Regioselective Cycloisomerization of Bis(indol-3-yl)-ynamides to Access Five-membered Ring Linked Bisindole Derivatives 金(I)催化双(吲哚-3-基)炔酰胺的区域选择性环异构化以获得五元环连接的双吲哚衍生物
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-10 DOI: 10.1002/adsc.202401052
Zhan-Shuai Xiao, Yin Wei, Min Shi
{"title":"Gold(I)-Catalyzed Regioselective Cycloisomerization of Bis(indol-3-yl)-ynamides to Access Five-membered Ring Linked Bisindole Derivatives","authors":"Zhan-Shuai Xiao, Yin Wei, Min Shi","doi":"10.1002/adsc.202401052","DOIUrl":"https://doi.org/10.1002/adsc.202401052","url":null,"abstract":"A gold(I)-catalyzed regioselective cycloisomerization of bis(indol-3-yl)-ynamides for the rapid construction of five-membered ring linked bisindole derivatives has been reported, affording the desired products in the range of 72% - 94% yields under mild conditions along with broad substrate scope. Moreover, DFT calculation of the NBO (natural bond orbital) charge supports the origin of its regioselectivity.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"70 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142597911","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
Construction of α‐ketoamides via Photoredox‐Catalyzed N−H Insertion of Amines by Sulfoxonium Ylides 通过光氧化催化亚磺酸铵N-H插入胺构建α-酮酰胺
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-08 DOI: 10.1002/adsc.202401020
Xianglin Yu, Haiyue Yang, Chang Liu, Qiping He, Zhijun Yang, Yi Jin
{"title":"Construction of α‐ketoamides via Photoredox‐Catalyzed N−H Insertion of Amines by Sulfoxonium Ylides","authors":"Xianglin Yu, Haiyue Yang, Chang Liu, Qiping He, Zhijun Yang, Yi Jin","doi":"10.1002/adsc.202401020","DOIUrl":"https://doi.org/10.1002/adsc.202401020","url":null,"abstract":"Herein, we report the development of photoredox‐catalyzed N−H insertion of sulfoxonium ylides with amines via oxidative single‐electron transfer (SET). These reactions exhibit broad substrate scope (32 examples) and offer operationally simple, scalable procedures for accessing α‐ketoamides in a single step. Mechanistic studies and control experiments confirm the participation of a photogenerated carbon radical in facilitating the oxidative single‐electron transfer (SET) from the sulfoxonium ylides to initiate the reaction.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142598075","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
Oxidative Photochemical Cyclisations to Access Spiroketals. 通过氧化光化学循环获得螺环酮。
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-07 DOI: 10.1002/adsc.202401264
Jonathan Trevorrow, Nhlanhla Sibanda, Anne O'Kearney‐McMullan, Lucie Miller Potucka, Adrian P. Dobbs
{"title":"Oxidative Photochemical Cyclisations to Access Spiroketals.","authors":"Jonathan Trevorrow, Nhlanhla Sibanda, Anne O'Kearney‐McMullan, Lucie Miller Potucka, Adrian P. Dobbs","doi":"10.1002/adsc.202401264","DOIUrl":"https://doi.org/10.1002/adsc.202401264","url":null,"abstract":"The front cover illustrates a novel photochemical cyclisation to prepare spiroketals and which was utilised to prepare a number of bee pheromone natural products. Details can be found in Research Article by Adrian P. Dobbs, and co-workers (J. Trevorrow, N. Sibanda, A. O'Kearney-McMullan, L. M. Potucka, A. P. Dobbs, <i>Adv. Synth. Catal</i>. <b>2024</b>, <i>366</i>, XXXX–XXXX; DOI: 10.1002/adsc.202400393)","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"63 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142598078","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
Sulfur (VI) Fluoride Exchange (SuFEx) via Glass–Assisted Organocatalysis 通过玻璃辅助有机催化实现硫 (VI) 氟化物交换 (SuFEx)
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-11-06 DOI: 10.1002/adsc.202401175
Ismat Nawaz, Maryam Nawaz, Rahman Shah Zaib Saleem, Ghayoor Abbas Chotana
{"title":"Sulfur (VI) Fluoride Exchange (SuFEx) via Glass–Assisted Organocatalysis","authors":"Ismat Nawaz, Maryam Nawaz, Rahman Shah Zaib Saleem, Ghayoor Abbas Chotana","doi":"10.1002/adsc.202401175","DOIUrl":"https://doi.org/10.1002/adsc.202401175","url":null,"abstract":"An environmentally benign route for the synthesis of sulfonamides via Sulfur (VI) Fluoride Exchange (SuFEx) chemistry utilizing N-methylimidazole, that simultaneously act as a base, precatalyst, HF by-product scavenger, as well as solvent, is described. This one-step sulfonamide synthesis exhibits excellent reactivity toward highly electron-deficient and less nucleophilic anilines as well as aminopyridines while tolerating a wide range of functional groups. In addition to the desired sulfonamide target, we also isolated an ionic salt as the sole side product from the reaction mixture that has been identified as bis[1-methyl-1H-imidazole-3-ium] hexafluorosilicate (IV). The glass surface of reaction vessel is acting as the source of silicon present in the isolated side product. Formation of hexafluorosilicate salt is also facilitating the consumption of sulfonyl fluoride for sulfonamide synthesis. Optimization of the reaction under various conditions, as well as the isolation of the bis[1-methyl-1H-imidazole-3-ium] hexafluorosilicate (IV) salt, highlight the crucial role of N-methylimidazole and support the glass-assisted approach. Besides the first example of glass-assisted SuFEx catalyzed by benign organic bases, this reaction also offers an alternative route for accessing protic hexafluorosilicate-based molten salts without employing external HF. The synthetic utility of this SuFEx route for late-stage functionalization is also demonstrated.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"64 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142589152","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
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&lt;sub&gt;3&lt;/sub&gt;SO&lt;sub&gt;2&lt;/sub&gt;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
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