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Photoinduced Charge-Transfer Complex Enables ortho-Fluorobenzamide C–F Bond Activation in Isoindolinone Synthesis 光诱导电荷转移配合物在异吲哚酮合成中激活邻氟苯酰胺C-F键
4区 化学
Synthesis-Stuttgart Pub Date : 2026-01-02 DOI: 10.1055/a-2773-5408
He Sheng, Xin Zhang, Xiang-Yu Chen
{"title":"Photoinduced Charge-Transfer Complex Enables ortho-Fluorobenzamide C–F Bond Activation in Isoindolinone Synthesis","authors":"He Sheng, Xin Zhang, Xiang-Yu Chen","doi":"10.1055/a-2773-5408","DOIUrl":"https://doi.org/10.1055/a-2773-5408","url":null,"abstract":"Abstract Photoinduced reactions of o-iodo, o-bromo, and o-chlorobenzamides have been well-established for the synthesis of isoindolinones; however, the corresponding fluorinated substrates remain underexplored. Herein, we report the photoactivation of fluorobenzamides via a novel charge-transfer complex (CTC) pathway, enabling the efficient synthesis of isoindolinone derivatives. Central to this approach is the formation of a CTC between the tBuOK/DMSO anion and fluorobenzamides under light irradiation. This method is operationally simple, mild, and provides a practical route for accessing isoindolinones.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"58 06","pages":"679-684"},"PeriodicalIF":0.0,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147887467","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
(E)-Selective Defluorinative Diphenothiazination of Trifluoromethyl Styrenes (E)-三氟甲基苯乙烯的选择性脱氟二吩噻嗪化
4区 化学
Synthesis-Stuttgart Pub Date : 2025-12-01 DOI: 10.1055/a-2735-9268
Yun Yang, Ben Ebel, Iris M. Oppel, Frédéric W. Patureau
{"title":"(E)-Selective Defluorinative Diphenothiazination of Trifluoromethyl Styrenes","authors":"Yun Yang, Ben Ebel, Iris M. Oppel, Frédéric W. Patureau","doi":"10.1055/a-2735-9268","DOIUrl":"https://doi.org/10.1055/a-2735-9268","url":null,"abstract":"Abstract Alpha-trifluoromethyl styrenes have become a versatile and valuable platform in order to access a wide variety of fluorinated organic motifs over recent years. This is due to their propensity to accommodate diverse defluorinative radical or nucleophilic attacks, which can lead to highly functionalized fluorinated alkenes. In some cases, such as described herein, E/Z selectivity issues can arise. While Zhu showed in 2021 that indole and carbazole nucleophiles lead preferentially to the (Z)-fluoroalkenes, we found that phenothiazines reverse the selectivity toward the (E)-configured diphenothiazinated fluoroalkenes. A scope and diastereoselectivity model for this unexpected reversal is discussed.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"58 06","pages":"632-638"},"PeriodicalIF":0.0,"publicationDate":"2025-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147899067","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
NaHBEt3-Catalyzed 1,2-Hydroboration of α,β-Unsaturated Carbonyls: Mechanistic Insights into Hydride Transfer Pathways nahbet3催化α，β-不饱和羰基的1,2-硼氢化反应：氢化物转移途径的机理研究
4区 化学
Synthesis-Stuttgart Pub Date : 2025-11-11 DOI: 10.1055/a-2744-6665
N. S. V. M. Rao Mangina, Sehoon Park
{"title":"NaHBEt3-Catalyzed 1,2-Hydroboration of α,β-Unsaturated Carbonyls: Mechanistic Insights into Hydride Transfer Pathways","authors":"N. S. V. M. Rao Mangina, Sehoon Park","doi":"10.1055/a-2744-6665","DOIUrl":"https://doi.org/10.1055/a-2744-6665","url":null,"abstract":"Abstract A highly 1,2-selective hydroboration of α,β-unsaturated ketones and aldehydes has been achieved by employing simple and readily available, transition metal-free NaHBEt3 as a catalyst. This sodium-catalyzed reaction proceeds at room temperature, exclusively furnishing the corresponding allylic alcohols with broad substrate scope and excellent functional group tolerance, including nitrile, amine, esters, nitro groups, alkoxy groups, and halides. Mechanistic studies suggest that (i) BEt3 serves as a Lewis acid cocatalyst, activating the substrate and facilitating the reaction, (ii) the resting hydride species are H2Bpin and (EtO)HBpin, and (iii) the rate-determining step involves hydride transfer from these resting species to the carbonyl carbon.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"58 04","pages":"441-448"},"PeriodicalIF":0.0,"publicationDate":"2025-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147916777","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Photocatalytic Regioselective Hydroboration of Indoles and Benzofurans with N-Heterocyclic Carbene Boranes n -杂环碳硼烷催化吲哚和苯并呋喃的区域选择性硼化反应
4区 化学
Synthesis-Stuttgart Pub Date : 2025-10-27 DOI: 10.1055/a-2733-4012
Yubing Pang, Zeyu Ma, Juntao Ye
{"title":"Photocatalytic Regioselective Hydroboration of Indoles and Benzofurans with N-Heterocyclic Carbene Boranes","authors":"Yubing Pang, Zeyu Ma, Juntao Ye","doi":"10.1055/a-2733-4012","DOIUrl":"https://doi.org/10.1055/a-2733-4012","url":null,"abstract":"Abstract Dearomative hydroboration of arenes using nucleophilic boryl radicals provides a powerful strategy for converting flat, abundant arenes into valuable, three-dimensional organoboron architectures. While such reactions are well established for electron-deficient arenes, the analogous transformation of electron-rich heteroarenes remains challenging due to a polarity mismatch. Herein, we report a photocatalytic approach that enables the regioselective, dearomative hydroboration of both electron-rich and electron-deficient indoles and benzofurans using N-heterocyclic carbene boranes. Density functional theory calculations indicate that the C2 addition of the boryl radical is kinetically favored over the C3 addition, and that the addition step becomes irreversible due to a subsequent, low-barrier hydrogen-atom-transfer event.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"58 02","pages":"195-203"},"PeriodicalIF":0.0,"publicationDate":"2025-10-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147893903","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
New Insight into the Photochromism of Spiropyrans: Substituent Effects on Equilibrium, Rate Constants, and Dipole Moments 螺吡喃的光致变色新认识：取代基对平衡、速率常数和偶极矩的影响
4区 化学
Synthesis-Stuttgart Pub Date : 2025-09-29 DOI: 10.1055/a-2701-5906
Niklas Hermes, Mascha Sirin Vogt, Vanessa Gruber, Rebecca F. Maier, Kimia Niazkar, Ralf Wolfgang Giernoth
{"title":"New Insight into the Photochromism of Spiropyrans: Substituent Effects on Equilibrium, Rate Constants, and Dipole Moments","authors":"Niklas Hermes, Mascha Sirin Vogt, Vanessa Gruber, Rebecca F. Maier, Kimia Niazkar, Ralf Wolfgang Giernoth","doi":"10.1055/a-2701-5906","DOIUrl":"https://doi.org/10.1055/a-2701-5906","url":null,"abstract":"Abstract Spiropyrans (SPs) and merocyanines (MCs) are among the most widely used photochromic systems today. Besides solvent polarity and temperature, the electronic properties of the substituents have a significant influence on photochromic behavior. In this work, a comprehensive study on the influences of electron-donating and -withdrawing substituents at the benzopyran as well as the indole moiety of the photochromic system are elucidated. For this purpose, changes in rate constants and the shift of the SP/MC equilibrium are investigated utilizing UV/vis and NMR spectroscopy. Based on DFT calculations, a relationship between these properties and the dipole moments of the molecules is established.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"58 01","pages":"32-40"},"PeriodicalIF":0.0,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147881183","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
A Chlorine-Bearing Asymmetric Center as a Stereocontrol Element in a Short Formal Synthesis of Steviol. 含氯不对称中心在甜菊糖短形式合成中的立体控制元件。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2025-09-04 DOI: 10.1055/a-2695-8576
Sharon E Michalak, Christopher D Vanderwal
{"title":"A Chlorine-Bearing Asymmetric Center as a Stereocontrol Element in a Short Formal Synthesis of Steviol.","authors":"Sharon E Michalak, Christopher D Vanderwal","doi":"10.1055/a-2695-8576","DOIUrl":"10.1055/a-2695-8576","url":null,"abstract":"<p><p>Steviol is one of myriad polycyclic terpenoids bearing oxygenation on the axially disposed C19 carbon. The presence of this C19 alcohol renders the C4 quaternary carbon stereogenic, issuing a challenge for stereoselective synthesis. Here we show that a suitably disposed chlorine atom at C2, coupled with the correct diastereomer of terminal epoxide that initiates cationic bicyclization, leads to the desired stereochemical outcome. Subsequently, the anisole terminating group undergoes Birch reduction that simultaneously reduces the C-Cl bond, removing the transient \"auxiliary\" and completing a short, highly stereoselective formal synthesis of steviol. This work provides another example of the power of removable C-X bonds for stereocontrolled synthesis.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" ","pages":""},"PeriodicalIF":2.2,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12456424/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145139288","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Reductive Monocarboxylation of Aryl Alkynes with CO2 via Electrochemistry 芳基炔与CO2的电化学还原单羧化反应
4区 化学
Synthesis-Stuttgart Pub Date : 2025-09-04 DOI: 10.1055/a-2695-8269
Zhihai Zhang, Shuping Zhu, Qianqian Wei, Jianyou Mao, Yanhua Zhang
{"title":"Reductive Monocarboxylation of Aryl Alkynes with CO2 via Electrochemistry","authors":"Zhihai Zhang, Shuping Zhu, Qianqian Wei, Jianyou Mao, Yanhua Zhang","doi":"10.1055/a-2695-8269","DOIUrl":"https://doi.org/10.1055/a-2695-8269","url":null,"abstract":"Abstract An electrochemical monocarboxylation of aryl alkynes with carbon dioxide to prepare acrylic acids and propionic acids has been developed. In a three-electrode electrochemical system, the reaction proceeds smoothly at a constant current in acetonitrile, which contains tetrabutylammonium bromide, and gives monocarboxylic acid products with up to 72% overall isolated yield. The system is applicable to terminal and internal aryl alkynes, exhibiting good functional group tolerance. This method may open up a window for the application of the electrochemical strategy in the synthesis of monocarboxylic acids from unsaturated hydrocarbons.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 24","pages":"3727-3733"},"PeriodicalIF":0.0,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147895333","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Unexpected Regiochemical Control in the Nugent-RajanBabu Reductive Epoxide Cyclization. Nugent-RajanBabu还原环氧化物环化过程中意想不到的区域化学控制。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2025-08-08 DOI: 10.1055/a-2680-2368
Nantamon Supantanapong, Scott W Niman, Christopher D Vanderwal
{"title":"Unexpected Regiochemical Control in the Nugent-RajanBabu Reductive Epoxide Cyclization.","authors":"Nantamon Supantanapong, Scott W Niman, Christopher D Vanderwal","doi":"10.1055/a-2680-2368","DOIUrl":"10.1055/a-2680-2368","url":null,"abstract":"<p><p>The Nugent-RajanBabu reductive epoxide cyclization has become a mainstay of alternative methods to accomplish classical, biomimetic, cationic polyene cyclizations. In most cases, the regiochemical control for the formation of decalins and perhydrophenanthrenes is exquisite, mirroring that obtained in cationic reactions, to the point where the 6-<i>endo</i> reactivity is anticipated even in the face of potential 5-<i>exo</i> processes. In our studies toward complex, polyoxygenated terpenoid natural products, we had cause to evaluate the reactions of α-alkoxy epoxides in these types of reactions, and we were surprised to uncover a means to control 6-<i>endo</i> vs 5-<i>exo</i> reactions based on the size of the protecting group on the α-oxygen. This knowledge opens up the possibility of rapid syntheses of highly oxygenated cyclopentane systems, in addition to the expected decalin scaffolds.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" ","pages":""},"PeriodicalIF":2.2,"publicationDate":"2025-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12456417/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145139261","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Nickel-Catalyzed Enantioconvergent C(sp3)–C(sp3) Cross-Coupling between α-Iodogermanes and Alkylzinc Reagents 镍催化α-碘日耳曼与烷基锌试剂间的对映收敛C(sp3) -C （sp3）交叉偶联
4区 化学
Synthesis-Stuttgart Pub Date : 2025-06-25 DOI: 10.1055/a-2643-6539
Emilio Gabriel Andreas Acuña Bolomey, Martin Oestreich
{"title":"Nickel-Catalyzed Enantioconvergent C(sp3)–C(sp3) Cross-Coupling between α-Iodogermanes and Alkylzinc Reagents","authors":"Emilio Gabriel Andreas Acuña Bolomey, Martin Oestreich","doi":"10.1055/a-2643-6539","DOIUrl":"https://doi.org/10.1055/a-2643-6539","url":null,"abstract":"Abstract We report a nickel-catalyzed enantioconvergent C(sp3)–C(sp3) cross-coupling between α-iodogermanes and alkylzinc reagents to access α-chiral alkylgermanes. This transformation, a strategy previously established for silicon-based electrophiles, extends to germanium, enabling the enantioselective formation of α-chiral germanes from simple, unactivated alkyl chains. While yields and enantioselectivities remain moderate, the reaction outcome was finely tuned through the design and evaluation of a library of over 30 ligands, including more than a dozen novel scaffolds. Notably, two distinct NiBr₂∙PyBox complexes allowed for access to products of opposite absolute configuration, and preformed nickel complexes were required to reach synthetically useful conversions. These findings highlight the challenges of asymmetric catalysis with heavier main-group elements and provide a platform for the future design of ligands tailored to organogermanium chemistry.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 21","pages":"3273-3282"},"PeriodicalIF":0.0,"publicationDate":"2025-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147913514","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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: 1
Ni-Catalyzed Regioselective Hydrodimerization of Enamides with Unactivated Alkenes 镍催化烯酰胺与非活化烯烃的区域选择性加氢二聚化反应
4区 化学
Synthesis-Stuttgart Pub Date : 2025-06-20 DOI: 10.1055/a-2640-2026
Qifa Chen, Qing Yan, Li Cheng, Yanhong Song, Hegui Gong
{"title":"Ni-Catalyzed Regioselective Hydrodimerization of Enamides with Unactivated Alkenes","authors":"Qifa Chen, Qing Yan, Li Cheng, Yanhong Song, Hegui Gong","doi":"10.1055/a-2640-2026","DOIUrl":"https://doi.org/10.1055/a-2640-2026","url":null,"abstract":"Abstract In this study, we described the Ni-catalyzed cross-hydrodimerization of enamides with unactivated alkenes under SiH/DTBP-mediated thermoredox conditions that was promoted by catalytic CuBr. The reaction afforded α-branched primary amines/secondary amides in good yields and with high regioselectivity through the formation of a C(sp3)–C(sp3) bond at the N-α-carbons. Excellent functional compatibility was observed across a wide range of sterically congested enamides and alkenes, including allylic branched enamides and 1,1-disubstituted alkenes. The use of chiral BiOx ligand enabled the formation of chiral amides with a high level of enantioselectivity. The present study offers a new entry for expediting the preparation of secondary amides appended to internal alkyl chains, complementing existing methods in the rapidly growing field of C(sp3)–C(sp3) bond construction via the hydrodimerization of two distinct alkenes.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 20","pages":"2977-2982"},"PeriodicalIF":0.0,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147912649","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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: 1
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