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Lewis Acid-Catalyzed Domino Inverse Electron-Demand Diels–Alder/Thermal Ring Expansion Reaction for the Synthesis of Arene-Annulated Eight-Membered Nitrogen Heterocycles Lewis酸催化的多米诺逆电按需diols - alder /热扩环反应合成芳烃环八元氮杂环
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01150
Michel Große, Christopher M. Leonhardt, Patrick A. R. Campbell, Hermann A. Wegner
{"title":"Lewis Acid-Catalyzed Domino Inverse Electron-Demand Diels–Alder/Thermal Ring Expansion Reaction for the Synthesis of Arene-Annulated Eight-Membered Nitrogen Heterocycles","authors":"Michel Große, Christopher M. Leonhardt, Patrick A. R. Campbell, Hermann A. Wegner","doi":"10.1021/acs.orglett.5c01150","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01150","url":null,"abstract":"A domino inverse electron-demand Diels–Alder reaction/thermal ring expansion sequence was developed to enable the one-step synthesis of arene-annulated eight-membered nitrogen heterocycles from readily available aromatic 1,2-diazines. A boron-based, bidentate Lewis acid catalyst facilitates the initial cycloaddition of Boc-protected 2-azetine with various electron-poor and electron-rich phthalazines. The subsequent electrocyclic ring expansion furnishes azocines fused to differently substituted aromatics, a structural motif that holds vast potential for further derivatization.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143893772","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 RhII-Catalyzed [4 + 3]-Cycloaddition via the Stereoselective Cyclopropanation of Vinyl Allenes En Route to Oxepino[b]indoles and Subsequent Elaboration to Spirooxindole Frameworks rhii催化的[4 + 3]-乙烯基烯的立体选择性环丙化加成制Oxepino[b]吲哚和随后的螺旋吲哚框架的精化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-05-01 DOI: 10.1021/acs.orglett.5c01329
Jiyoon Kim, Kevin X. Rodriguez, Kaitlyn E. Eckert, Allen G. Oliver, Brandon L. Ashfeld
{"title":"A RhII-Catalyzed [4 + 3]-Cycloaddition via the Stereoselective Cyclopropanation of Vinyl Allenes En Route to Oxepino[b]indoles and Subsequent Elaboration to Spirooxindole Frameworks","authors":"Jiyoon Kim, Kevin X. Rodriguez, Kaitlyn E. Eckert, Allen G. Oliver, Brandon L. Ashfeld","doi":"10.1021/acs.orglett.5c01329","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01329","url":null,"abstract":"Oxepino[<i>b</i>]indoles were obtained in good to excellent yields employing a [4 + 3]-cycloaddition initiated by a stereo- and regioselective, Rh<sup>II</sup>-catalyzed cyclopropanation between a vinyl allene and diazooxindole to afford an intermediate cyclopropyl allene that engaged the oxindole carbonyl in a spontaneous hetero-[3,3]-rearrangement. A survey of functional group tolerance revealed a diverse array of substrates amenable to oxepino[<i>b</i>]indole formation. In addition to the intriguing architecture of the cycloadducts, exposure to either Brønsted acid or base enables the assembly of functionalized spirroxindoles via the unusual conversion of a 5–7 fused ring system to a 5–5 spirocycle.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"96 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897967","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
Transition-Metal Free Photocatalytic Synthesis of Acylsulfonamides 无过渡金属光催化合成酰基磺酰胺
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-30 DOI: 10.1021/acs.orglett.5c01129
Long Yin Lam, Cong Ma
{"title":"Transition-Metal Free Photocatalytic Synthesis of Acylsulfonamides","authors":"Long Yin Lam, Cong Ma","doi":"10.1021/acs.orglett.5c01129","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01129","url":null,"abstract":"We have developed a transition-metal-free photocatalytic S–N coupling reaction utilizing sodium organosulfinate and hydroxamic acid to synthesize acylsulfonamides. Employing 2,3,5,6-tetra(9H-carbazol-9-yl)benzonitrile (4CzBN) as a photocatalyst, this method enables the preparation of a wide range of acylsulfonamides from arylhydroxamic acids or <i>N</i>-hydroxycarbamates. Mechanistic studies indicate that the generation of singlet oxygen (<sup>1</sup>O<sub>2</sub>) via the Energy Transfer Process (EnT) is crucial for facilitating the reaction. This approach offers a sustainable and efficient pathway for acylsulfonamide synthesis under mild conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"47 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143893774","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
Hypervalent Iodine-Mediated Selective Monofunctionalization of Calix[4]arenes 高价碘介导杯萼芳烃选择性单功能化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-30 DOI: 10.1021/acs.orglett.5c01121
Haoliang Hao, Wei Zhang, Wenjie Zhu, Wenjing Bao, Guangxing Gu, Yanchuan Zhao
{"title":"Hypervalent Iodine-Mediated Selective Monofunctionalization of Calix[4]arenes","authors":"Haoliang Hao, Wei Zhang, Wenjie Zhu, Wenjing Bao, Guangxing Gu, Yanchuan Zhao","doi":"10.1021/acs.orglett.5c01121","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01121","url":null,"abstract":"The selective introduction of a single functionality on the upper rim of calix[4]arene is challenging due to the identical reactivity of its four aryl units. In this study, we introduce a novel strategy for monofunctional modification of calix[4]arenes using a hypervalent iodine-mediated C–H functionalization. This process yields a calix[4]arene-iodonium salt, which can be easily isolated due to its distinct solubility compared to the native calixarene. This versatile intermediate efficiently undergoes C–O, C–N, and C–S couplings with a variety of nucleophiles, including amines, phenols, thiols, and sulfinate salts under mild conditions. This strategy enables streamlined structural diversification of calix[4]arenes, opening new avenues for the design of supramolecular macrocycles with tailored functions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"35 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890199","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
Quinol–Enedione Rearrangement Quinol-Enedione重排
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-30 DOI: 10.1021/acs.orglett.5c01266
Tomás Vieira de Castro, François Richard, Steven H. Bennett, Caspar S. Lamborelle, Gary S. Nichol, Rafał Szabla, Andrew L. Lawrence
{"title":"Quinol–Enedione Rearrangement","authors":"Tomás Vieira de Castro, François Richard, Steven H. Bennett, Caspar S. Lamborelle, Gary S. Nichol, Rafał Szabla, Andrew L. Lawrence","doi":"10.1021/acs.orglett.5c01266","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01266","url":null,"abstract":"The quinol–enedione rearrangement enables the synthesis of 2-cyclohexene-1,4-diones from readily available <i>para</i>-quinol substrates. Building on sporadic early reports of this transformation, we have optimized the reaction conditions and systematically investigated its substrate scope. The utility of Brønsted acid-mediated reaction conditions for a variety of quinol derivatives, including those with substituted and unsubstituted migrating termini, is highlighted. Notably, kinetic selectivity between quinol–enedione and dienone–phenol rearrangements is demonstrated. The synthetic potential of the enedione products is showcased through a range of transformations, leading to the formation of complex polycyclic structures. These findings provide a valuable framework for recognizing and applying the quinol–enedione rearrangement in synthesis, while computational studies offer valuable insights into its mechanistic underpinnings.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"44 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890212","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
Total Syntheses of Plocabulin and Its C2-Analogues Plocabulin及其c2类似物的全合成
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-30 DOI: 10.1021/acs.orglett.5c01284
Shunfa Liu, Bin Li, Xin Gao, Fenglin Wang, Xuan Li, Juxi Wang, Yuzhong Kuang, Luai Ji, Lu Gao, Wanshu Wang, Qifeng Chen, Yong Qin, Zhenlei Song
{"title":"Total Syntheses of Plocabulin and Its C2-Analogues","authors":"Shunfa Liu, Bin Li, Xin Gao, Fenglin Wang, Xuan Li, Juxi Wang, Yuzhong Kuang, Luai Ji, Lu Gao, Wanshu Wang, Qifeng Chen, Yong Qin, Zhenlei Song","doi":"10.1021/acs.orglett.5c01284","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01284","url":null,"abstract":"Plocabulin is a structurally unique marine natural product with potent antitumor activity, making it a promising candidate for the development of antibody–drug conjugates (ADCs). However, its extremely low natural abundance has limited further research and therapeutic exploration. In this study, we present a convergent synthetic strategy for plocabulin and its C2-analogues. Our approach enabled the synthesis of 1.23 g of plocabulin through a longest linear sequence of 12 steps and a total of 24 steps, achieving an overall yield of 19.7%.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143893775","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
Interlocking Pseudorotaxanes through Borane- and Boronic Ester-Mediated Carbon–Carbon Bond Formation 通过硼烷和硼酯介导的碳-碳键形成联锁假环烷
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-30 DOI: 10.1021/acs.orglett.5c01233
Jia-Jyun Jian, Min-Xuan Zhang, Yi-Hung Liu, Sheng-Hsien Chiu
{"title":"Interlocking Pseudorotaxanes through Borane- and Boronic Ester-Mediated Carbon–Carbon Bond Formation","authors":"Jia-Jyun Jian, Min-Xuan Zhang, Yi-Hung Liu, Sheng-Hsien Chiu","doi":"10.1021/acs.orglett.5c01233","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01233","url":null,"abstract":"Employing 9-BBN and pinacol boronic ester as surrogate stoppers, pseudorotaxanes presenting terminal alkenes can be transformed into organoborane or organoboronate rotaxanes, respectively. Various boron-based reactions can then be used to replace these temporary stoppers with bulky derivatives of aromatic bromides, α-bromo ketones, or 1-bromo-1-alkynes, facilitating the selective formation of sp<sup>3</sup>–sp<sup>2</sup>, sp<sup>3</sup>–sp<sup>3</sup>, and sp<sup>3</sup>–sp carbon–carbon single bonds, respectively.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"20 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890255","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
Visible-Light-Driven Catalytic Alkylation of Reactive Alkyl Nitriles with Nonactivated Alkenes Using an Amine as a Hydrogen Atom Transfer Catalyst 用胺作氢原子转移催化剂催化活性烷基腈与非活化烯烃的可见光催化烷基化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-30 DOI: 10.1021/acs.orglett.5c01072
Yuki Sato, Tomoya Hisada, Yasuhiro Yamashita, Shu̅ Kobayashi
{"title":"Visible-Light-Driven Catalytic Alkylation of Reactive Alkyl Nitriles with Nonactivated Alkenes Using an Amine as a Hydrogen Atom Transfer Catalyst","authors":"Yuki Sato, Tomoya Hisada, Yasuhiro Yamashita, Shu̅ Kobayashi","doi":"10.1021/acs.orglett.5c01072","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01072","url":null,"abstract":"We have developed a photoinduced catalytic alkylation reaction of reactive alkyl nitriles with nonactivated alkenes using a simple amine as a hydrogen atom transfer (HAT) catalyst. This reaction proceeds smoothly under mild reaction conditions with blue LED irradiation to afford a variety of alkylated nitriles. Not only were unactivated alkenes employable but also styrene derivatives. The key to success of this reaction is the generation of an electrophilic alkyl radical species from alkyl nitrile. The use of a readily available amine catalyst such as <i>N</i>,<i>N</i>-dialkylanilines is effective to promote this reaction efficiently.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"69 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890196","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
Photoinduced Site-Selective Alkylation Enabling Synthesis of C-3-Alkylated Quinoxalinone on DNA 光诱导选择性烷基化在DNA上合成c -3-烷基化喹啉酮
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-30 DOI: 10.1021/acs.orglett.5c01236
Kyeong Seop Kim, Junseok Ra, Madala Hari Babu, Eunbin Jang, Seohyeon Kang, Minhyeok Yoo, Thinh T. M. Bui, Kyuho Moon, Jaehoon Sim
{"title":"Photoinduced Site-Selective Alkylation Enabling Synthesis of C-3-Alkylated Quinoxalinone on DNA","authors":"Kyeong Seop Kim, Junseok Ra, Madala Hari Babu, Eunbin Jang, Seohyeon Kang, Minhyeok Yoo, Thinh T. M. Bui, Kyuho Moon, Jaehoon Sim","doi":"10.1021/acs.orglett.5c01236","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01236","url":null,"abstract":"A mild and biocompatible strategy for the site-selective alkylation of quinoxalinones via photoinduced dehydrogenative alkylation has been developed. This protocol enables the functionalization of both unprotected quinoxalinone and nonreactive dihydroquinoxalinone under DNA-compatible conditions. The optimized reaction proceeds efficiently while tolerating a diverse range of alkyl donors from various radical precursors. Given its simplicity and DNA compatibility, this methodology offers a platform for the construction of DNA-encoded libraries incorporating a privileged quinoxalinone scaffold.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"55 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890198","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
Cascade Reaction of Isocyanides with Carboxylic Acid and CD3SSO3Na: Toward S-CD3 Thiocarbamates 异氰酸酯与羧酸和CD3SSO3Na级联反应制备S-CD3硫代氨基甲酸酯
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-29 DOI: 10.1021/acs.orglett.5c01166
Xinyu Zhou, Kemeng Zhang, Shuodan Ding, Lijin Wang, Miaoying Li, Ke Wang, Jie Zhou, Ge Wu
{"title":"Cascade Reaction of Isocyanides with Carboxylic Acid and CD3SSO3Na: Toward S-CD3 Thiocarbamates","authors":"Xinyu Zhou, Kemeng Zhang, Shuodan Ding, Lijin Wang, Miaoying Li, Ke Wang, Jie Zhou, Ge Wu","doi":"10.1021/acs.orglett.5c01166","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01166","url":null,"abstract":"We developed an unprecedented cascade reaction involving isocyanides with carboxylic acids and CD<sub>3</sub>SSO<sub>3</sub>Na to access <i>S</i>-CD<sub>3</sub> thiocarbamates with the formation of two C–N bonds and one C–S bond. Preliminary mechanistic investigations disclose that these three-component reactions precede the esterification of carboxylic acids with isocyanides, generating a capable <i>N</i>-alkyl-<i>N</i>-formyl amide followed by thiolation with CD<sub>3</sub>SSO<sub>3</sub>Na to provide the corresponding products. The transformation has outstanding features in mild reaction conditions, effortless experimental operation, structural modification of polyfunctional carboxylic acid drugs, and large-scale preparation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143885414","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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