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Exploration of Glycosyl Dithioimidocarbonates in Photoinduced Desulfurative Cross-Coupling Reactions. 探索光诱导脱硫交叉偶联反应中的糖基二硫代亚硫酰碳酸酯。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 Epub Date: 2024-09-30 DOI: 10.1021/acs.orglett.4c03035
Ji Zhang, Qi Liu, Angus Chiang, Mark Nitz
{"title":"Exploration of Glycosyl Dithioimidocarbonates in Photoinduced Desulfurative Cross-Coupling Reactions.","authors":"Ji Zhang, Qi Liu, Angus Chiang, Mark Nitz","doi":"10.1021/acs.orglett.4c03035","DOIUrl":"10.1021/acs.orglett.4c03035","url":null,"abstract":"<p><p>Readily synthesized bench-stable glycosyl dithioimidocarbonates are useful <i>C</i>-glycoside precursors. Under mild photochemical conditions, these glycosides undergo desulfurative glycosyl radical generation in the presence of weak acid, 4CzIPN, and Hantzsch ester. These radicals perform well in Geise-like reactions to yield <i>C</i>-glycosides with high stereoselectivity.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142337308","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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-Heterocyclic Carbene Catalysis for Polycyclic Benzazepines Assembly: Regioselective Intramolecular Tandem Radical Cyclization. N-Heterocyclic Carbene Catalysis for Polycyclic Benzazepines Assembly：区域选择性分子内串联自由基环化。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 DOI: 10.1021/acs.orglett.4c03303
Zhiming Feng, Lili Wu, Cong-Ying Zhou, Chengming Wang
{"title":"N-Heterocyclic Carbene Catalysis for Polycyclic Benzazepines Assembly: Regioselective Intramolecular Tandem Radical Cyclization.","authors":"Zhiming Feng, Lili Wu, Cong-Ying Zhou, Chengming Wang","doi":"10.1021/acs.orglett.4c03303","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03303","url":null,"abstract":"<p><p>A variety of polycyclic benzazepines were rapidly constructed by NHC-catalyzed regioselective redox-neutral intramolecular tandem cyclization. Initial mechanistic studies revealed that a SET radical process was possibly involved.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398664","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 General Entry to Ganoderma Meroterpenoids: Synthesis of Applanatumol E, H, and I, Lingzhilactone B, Meroapplanin B, and Lingzhiol. 灵芝 Meroterpenoids 的一般入口：Applanatumol E、H 和 I、Lingzhilactone B、Meroapplanin B 和 Lingzhiol 的合成。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 DOI: 10.1021/acs.orglett.4c03192
Alexander Rode, Nicolas Müller, Ondřej Kováč, Klaus Wurst, Thomas Magauer
{"title":"A General Entry to <i>Ganoderma</i> Meroterpenoids: Synthesis of Applanatumol E, H, and I, Lingzhilactone B, Meroapplanin B, and Lingzhiol.","authors":"Alexander Rode, Nicolas Müller, Ondřej Kováč, Klaus Wurst, Thomas Magauer","doi":"10.1021/acs.orglett.4c03192","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03192","url":null,"abstract":"<p><p><i>Ganoderma</i> meroterpenoids are fungal derived hybrid natural product class containing a 1,2,4-trisubstituted benzene ring and a polycyclic terpenoid part. The representatives applanatumol E, H and I, lingzhilactone B, and meroapplanin B share the same bicyclic lactone moiety connected to the arene. Employing photo-Fries rearrangements as the key step enabled a general entry to these natural products. For the synthesis of the tetracyclic framework of lingzhiol, we made use of a powerful photoredox oxidative decarboxylation/Friedel-Crafts sequence.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142405720","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Introduction of the Trifluoropropionate Moiety into Aromatic Rings via Rhodium-Catalyzed Coupling of Arylboronic Acids with Diazoesters. 通过铑催化芳基硼酸与重氮酯的偶联，将三氟丙酸酯分子引入芳香环。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 Epub Date: 2024-10-01 DOI: 10.1021/acs.orglett.4c03190
Jogendra Kumar, Sourav Manna, Lukas J Gooßen
{"title":"Introduction of the Trifluoropropionate Moiety into Aromatic Rings via Rhodium-Catalyzed Coupling of Arylboronic Acids with Diazoesters.","authors":"Jogendra Kumar, Sourav Manna, Lukas J Gooßen","doi":"10.1021/acs.orglett.4c03190","DOIUrl":"10.1021/acs.orglett.4c03190","url":null,"abstract":"<p><p>A catalytic method for the introduction of pharmaceutically meaningful fluorinated propionic acid side chains into aromatic compounds is presented. In the presence of rhodium catalyst [RhCp*Cl<sub>2</sub>]<sub>2</sub>, various arylboronic acids are efficiently coupled with an easy-to-access diazoester reagent to give perfluorinated derivatives of phenylpropionic acids, including top-selling profen drugs. The key advantage of this approach is that the pharmacophore is introduced as a whole and is compatible with various functionalities and drug discovery.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142337309","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines. 利用成对电催化将亚磺酰胺与烯烃进行交叉偶联以合成乙烯基亚磺酰亚胺。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 Epub Date: 2024-10-02 DOI: 10.1021/acs.orglett.4c02859
Tao Liu, Yan Tang, Jiyuan Guo, Yunfei Hang, Kali Zhang, Changdi Zheng, Weihui Zhong, Dingguo Song, Fei Ling
{"title":"Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines.","authors":"Tao Liu, Yan Tang, Jiyuan Guo, Yunfei Hang, Kali Zhang, Changdi Zheng, Weihui Zhong, Dingguo Song, Fei Ling","doi":"10.1021/acs.orglett.4c02859","DOIUrl":"10.1021/acs.orglett.4c02859","url":null,"abstract":"<p><p>We present here a novel paired electrocatalysis-enabled convenient synthesis of the (<i>E</i>)-vinyl sulfoximines through the cross-coupling reaction of sulfinamides and olefins. This protocol showed a broad substrate scope and excellent <i>E</i> selectivity of products under metal- and oxidant-free conditions. A preliminary mechanistic study suggested that fluorinated sulfoximine generated from anodic oxidation of sulfinamide was the key intermediate that was then converted into the sulfonimidoyl radical at the cathode with the help of DBU in this reaction.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360764","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Conversion of Carboxylic Acids to Sulfonamide Bioisosteres via Energy Transfer Photocatalysis. 通过能量转移光催化将羧酸转化为磺酰胺生物异养生物。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 Epub Date: 2024-10-01 DOI: 10.1021/acs.orglett.4c03325
Zhipeng Zong, Jingjing Yang, Lulu Yuan, Xiaojie Wang, Jian-Qiang Chen, Jie Wu
{"title":"Conversion of Carboxylic Acids to Sulfonamide Bioisosteres via Energy Transfer Photocatalysis.","authors":"Zhipeng Zong, Jingjing Yang, Lulu Yuan, Xiaojie Wang, Jian-Qiang Chen, Jie Wu","doi":"10.1021/acs.orglett.4c03325","DOIUrl":"10.1021/acs.orglett.4c03325","url":null,"abstract":"<p><p>More than 450 drugs containing a carboxylic acid functional group have been marketed worldwide. Herein, we report a concise and environmentally friendly organic photoinduced protocol for the interconversion of carboxylic acids into their bioisosteres. With this strategy, a variety of substrates, including alkyl, (hetero)aryl, and alkenyl acids, as well as various biologically relevant acids are successfully converted into primary sulfonamides.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142337307","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Introducing Alkyl Selenocyanates as Bifunctional Reagents in Photoredox Catalysis: Divergent Access to Ambident Isomers of -SeCN. 引入烷基硒氰酸酯作为光氧化催化中的双功能试剂：烷基硒氰酸酯作为双功能试剂在光氧化催化中的应用：对-SeCN 的歧化异构体的不同访问。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 Epub Date: 2024-08-22 DOI: 10.1021/acs.orglett.4c02430
Shyamal Pramanik, Avik Kr Das, Saradindu Debnath, Soumitra Maity
{"title":"Introducing Alkyl Selenocyanates as Bifunctional Reagents in Photoredox Catalysis: Divergent Access to Ambident Isomers of -SeCN.","authors":"Shyamal Pramanik, Avik Kr Das, Saradindu Debnath, Soumitra Maity","doi":"10.1021/acs.orglett.4c02430","DOIUrl":"10.1021/acs.orglett.4c02430","url":null,"abstract":"<p><p>Owing to their diverse biological activities and versatility as synthetic precursors, organoselonocyanes categorize themselves as vital compounds. However, a limited reagent pool restricts their utility. In the present work, alkyl selenocyanates are hereby established as new bifunctional reagents for the simultaneous transfer of an alkyl group in addition to -SeCN. These reagents, when merged with photocatalysis, provide a key to accessing organoselenocyanates from feedstock olefins in an efficient and atom-economic fashion. A route to the analogous isoselenocyanate isomers facilitated by Lewis acid catalysis is also reported, presenting a divergent strategy for accessing both ambident isomers of -SeCN in an efficient manner.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142015578","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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-Promoted Chemodivergent Construction of 2H-Chromen-2-one and Chromeno[2,3-c]pyrrole Scaffolds from para-Quinone Methides and α-Alkylidene Succinimides. 由对位醌甲酰胺和α-亚烷基琥珀酰亚胺在碱促进下构建 2H-色烯-2-酮和色烯并[2,3-c]吡咯支架的化学发散作用。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 DOI: 10.1021/acs.orglett.4c03436
Km Roshani, Mohammad Saim Raza, Rama Krishna Peddinti
{"title":"Base-Promoted Chemodivergent Construction of 2<i>H</i>-Chromen-2-one and Chromeno[2,3-<i>c</i>]pyrrole Scaffolds from <i>para</i>-Quinone Methides and α-Alkylidene Succinimides.","authors":"Km Roshani, Mohammad Saim Raza, Rama Krishna Peddinti","doi":"10.1021/acs.orglett.4c03436","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03436","url":null,"abstract":"<p><p>Herein, we evolve a base-promoted synthesis of 2<i>H</i>-chromen-2-one and chromeno[2,3-<i>c</i>]pyrrole scaffolds via (4 + 2) annulation of α-alkylidene succinimides with 2-hydroxyphenyl-substituted <i>para</i>-quinone methides (<i>p</i>-QMs). Extremely selective and switchable cyclizations were obtained by modifying the base. This metal-free protocol is highlighted by its mild reaction conditions and broad substrate scope, and the viability of the existing protocol was additionally illustrated by gram-scale synthesis and further modification. Several control experiments were performed to understand the reaction mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142405721","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Unified Synthesis of Electron-Deficient 1,4- and 1,1,4-Substituted 1,3-Dienes through a Base-Promoted Allylation Followed by Retro-Michael Vinylogous Dehydrosulfinylation. 通过碱促进的烯丙基化和逆迈克尔乙烯基脱氢亚硫酰化统一合成缺电子的 1,4- 和 1,1,4- 取代的 1,3- 二烯。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 Epub Date: 2024-10-02 DOI: 10.1021/acs.orglett.4c03189
Ayelet Rothstein, Lena Trifonov, Niv Keidar, Michal Afri, Edward E Korshin, Arie Gruzman
{"title":"A Unified Synthesis of Electron-Deficient 1,4- and 1,1,4-Substituted 1,3-Dienes through a Base-Promoted Allylation Followed by <i>Retro</i>-Michael Vinylogous Dehydrosulfinylation.","authors":"Ayelet Rothstein, Lena Trifonov, Niv Keidar, Michal Afri, Edward E Korshin, Arie Gruzman","doi":"10.1021/acs.orglett.4c03189","DOIUrl":"10.1021/acs.orglett.4c03189","url":null,"abstract":"<p><p>We disclose a general 2-step synthesis of electron-poor 1,4- and 1,1,4-substituted buta-1,3-dienes bearing electron-withdrawing substituents at both termini of the conjugated system. The method relies on a base-promoted C-allylation of primary or secondary alkylsulfones with γ-bromocrotonate or related amide, nitrile, or sulfone and subsequent vinylogous <i>retro</i>-Michael dehydrosulfinylation. The geometry of the resulting dienes is substrate-dependent, and predominantly <i>E</i>,<i>E</i>-dienes are formed from <i>E</i>-electrophiles. This phosphorus- and transition-metal-free method tolerates a variety of functionalities and could serve as a supplement to Wittig, HWE, and Julia olefinations.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360763","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Palladium-Catalyzed Carbonylative Cyclization of 1-Alkynyl-2-iodo-d-glucal. 钯催化的 1-炔基-2-碘-d-葡萄糖醛的羰基环化反应。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-10-11 Epub Date: 2024-09-30 DOI: 10.1021/acs.orglett.4c03337
Milene M Hornink, Giuseppe E Figlino, Mônica F Z J Toledo, Daniel C Pimenta, Hélio A Stefani
{"title":"Palladium-Catalyzed Carbonylative Cyclization of 1-Alkynyl-2-iodo-d-glucal.","authors":"Milene M Hornink, Giuseppe E Figlino, Mônica F Z J Toledo, Daniel C Pimenta, Hélio A Stefani","doi":"10.1021/acs.orglett.4c03337","DOIUrl":"10.1021/acs.orglett.4c03337","url":null,"abstract":"<p><p>Cascade reactions are important synthetic tools for the synthesis of heterocyclic molecules, particularly those catalyzed by palladium. Herein, we report a palladium-catalyzed aminocarbonylative cyclization of new 1-alkynyl-2-iodo-d-glucals, which undergo a tandem carbonylative cyclization in the presence of various amine nucleophiles. A broad range of aromatic and aliphatic amines were applied as coupling partners, resulting in the selective and high-yield synthesis of glycosides fused to pyridinones. A plausible mechanism is proposed, proceeding via a tandem palladium aminocarbonylation followed by a palladium-catalyzed <i>endo-dig</i> cyclization.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142337310","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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