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Four-Component Radical 1,2-Selenosulfonylation of Allenes.
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-27 DOI: 10.1021/acs.orglett.4c01798
Xiao-Rong Shu, Mu-Han Li, Cuiyan Wu, Xi-Ni Luo, Dong-Qing Yang, Ming-Qi Yang, Yue-Jiao Lu, Guo-Ping Ge, Jidan Liu, Wen-Ting Wei
{"title":"Four-Component Radical 1,2-Selenosulfonylation of Allenes.","authors":"Xiao-Rong Shu, Mu-Han Li, Cuiyan Wu, Xi-Ni Luo, Dong-Qing Yang, Ming-Qi Yang, Yue-Jiao Lu, Guo-Ping Ge, Jidan Liu, Wen-Ting Wei","doi":"10.1021/acs.orglett.4c01798","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01798","url":null,"abstract":"<p><p>Selenosulfones, as pivotal pharmaceutical molecule frameworks, have become a research hotspot in modern organic synthesis due to their vital need for efficient preparation. Herein, we have developed an iron-catalyzed four-component controllable radical tandem reaction of allenes involving cycloketone oxime esters, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), and diphenyl diselenides for the synthesis of complex selenosulfones. This is the first case of achieving the 1,2-selenosulfonylation of allenes via a radical process, wherein precise control of radical rates and polarity matching enhance high regioselective conversion. The reaction conditions are ecofriendly and mild with step-efficiency by forming two new C-S bonds and one C-Se bond in one pot. Moreover, the 1,2-selenosulfonylation of allenes can be achieved by replacing cycloketone oxime esters with aryldiazonium tetrafluoroborates in this system.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453751","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
Regioselective Halogenation of Lavanducyanin by a Site-Selective Vanadium-Dependent Chloroperoxidase.
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-27 DOI: 10.1021/acs.orglett.4c01869
Jackson T Baumgartner, Shaun M K McKinnie
{"title":"Regioselective Halogenation of Lavanducyanin by a Site-Selective Vanadium-Dependent Chloroperoxidase.","authors":"Jackson T Baumgartner, Shaun M K McKinnie","doi":"10.1021/acs.orglett.4c01869","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01869","url":null,"abstract":"<p><p>Halogenated phenazine meroterpenoids are a structurally unusual family of marine actinobacterial natural products that exhibit antibiotic, antibiofilm, and cytotoxic bioactivities. Despite a lack of established phenazine halogenation biochemistry, genomic analysis of <i>Streptomyces</i> sp. CNZ-289, a prolific lavanducyanin and C2-halogenated derivative producer, suggested the involvement of vanadium-dependent haloperoxidases. We subsequently discovered lavanducyanin halogenase (LvcH), characterized it <i>in vitro</i> as a regioselective vanadium-dependent chloroperoxidase, and applied it in late-stage chemoenzymatic synthesis.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453755","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
Merging Quinoxalin-2(1H)-ones Excitation with Cobaloxime Catalysis: C3 Alkylation of Quinoxalin-2(1H)-ones with Unactivated Alkyl Iodides and Carboxylic Acids under Light.
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-27 DOI: 10.1021/acs.orglett.4c02021
Shuo Cao, Jia-Xin Chen, Xiu-Li Zhang, Xian Song, Wen-Yu Song, Yu-Sheng Wu, Yan-Hui Zhang, Zan Liu
{"title":"Merging Quinoxalin-2(1<i>H</i>)-ones Excitation with Cobaloxime Catalysis: C3 Alkylation of Quinoxalin-2(1<i>H</i>)-ones with Unactivated Alkyl Iodides and Carboxylic Acids under Light.","authors":"Shuo Cao, Jia-Xin Chen, Xiu-Li Zhang, Xian Song, Wen-Yu Song, Yu-Sheng Wu, Yan-Hui Zhang, Zan Liu","doi":"10.1021/acs.orglett.4c02021","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c02021","url":null,"abstract":"<p><p>Reported herein is a practical, economical, and efficient construction of 3-alkylated quinoxalin-2(1<i>H</i>)-ones with alkyl carboxylic acids and alkyl iodides by quinoxalin-2(1<i>H</i>)-one excitation and cobaloxime catalysis. Primary, secondary, and tertiary alkyl iodides and carboxylic acids all could be efficiently transferred into target products with excellent functional group tolerance. Mechanism studies reveal that the quinoxalin-2(1<i>H</i>)-one derivatives could be directly excited and yield alkyl carbon radicals from alkyl carboxylic acids and alkyl iodides with the aid of the cobaloxime complex.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453753","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
Heteroannulation of Arynes with α-Bromodifluorohydroxamates: An Efficient and General Approach to Access 2,2-Difluoro Indoxyls. α-溴二氟羟肟酸异annulation of Arynes with α-Bromodifluorohydroxamates：获得 2,2-二氟吲哚肟的高效通用方法。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-27 DOI: 10.1021/acs.orglett.4c01720
Deeksha, Ritesh Singh
{"title":"Heteroannulation of Arynes with α-Bromodifluorohydroxamates: An Efficient and General Approach to Access 2,2-Difluoro Indoxyls.","authors":"Deeksha, Ritesh Singh","doi":"10.1021/acs.orglett.4c01720","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01720","url":null,"abstract":"<p><p>Herein, we report the first general approach to access <i>N</i>-alkoxy-2,2-difluoro indoxyls, via formal 3 + 2 cycloaddition of aryne and (putative) fluorinated-aza-oxyallyl cation. This transition-metal/oxidant-free transformation occurs under mild reaction conditions with a short reaction time. Mechanistic investigation indicates the possible involvement of the closed form of fluorinated-aza-oxyallyl cation, viz., α-lactam, in the current transformation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453752","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
Regioselective Hydroboration of Unsymmetrical Internal Alkynes Catalyzed by a Cobalt Pincer-NHC Complex.
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-27 DOI: 10.1021/acs.orglett.4c02216
Naresh Kumar Meher, Maruti Suryavansi, K Geetharani
{"title":"Regioselective Hydroboration of Unsymmetrical Internal Alkynes Catalyzed by a Cobalt Pincer-NHC Complex.","authors":"Naresh Kumar Meher, Maruti Suryavansi, K Geetharani","doi":"10.1021/acs.orglett.4c02216","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c02216","url":null,"abstract":"<p><p>Highly regioselective hydroboration of unsymmetrical internal alkynes remains a significant challenge for synthesizing valuable alkenylboronate esters. Herein, we describe an easily synthesizable pincer NHC-based Co complex as a catalyst for the <i>cis</i>-α selective hydroboration of unactivated internal alkynes and the <i>cis</i>-β selective hydroboration of activated internal alkynes with pinacolborane. The reaction showcases high chemo-, regio-, and stereoselectivity, and the catalyst displays high efficiency and very low loading under base-free reaction conditions. The reaction scope was demonstrated by alkynes having a variety of functional groups. The mechanistic studies suggest a feasible Co-boryl intermediate to explain the unusual regioselectivity.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453756","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
Development of SF6 as a Formal Electrophilic Fluorinating Reagent for Photocatalyzed Oxidative Fluorination of Phosphine Oxides.
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-27 DOI: 10.1021/acs.orglett.4c01953
Yu-Ling Huang, Qing-Qing Zhang, Cheng-Yu Wang, Yue Zhao, Xi-Sheng Wang
{"title":"Development of SF<sub>6</sub> as a Formal Electrophilic Fluorinating Reagent for Photocatalyzed Oxidative Fluorination of Phosphine Oxides.","authors":"Yu-Ling Huang, Qing-Qing Zhang, Cheng-Yu Wang, Yue Zhao, Xi-Sheng Wang","doi":"10.1021/acs.orglett.4c01953","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01953","url":null,"abstract":"<p><p>Organophosphorus-fluorine compounds are of significant utility across biology, pharmacy, and chemical synthesis. Here, we introduce a photocatalyzed oxidative-fluorination approach employing SF<sub>6</sub> as a formal electrophilic fluorinating reagent. It offers an innovative pathway to forge P(O)-F bonds. Notably, sulfur hexafluoride plays a dual role as both the oxidant and the fluorinating reagent under mild conditions in this transformation. Meanwhile, this method contributes to environmental sustainability by consuming a notorious greenhouse gas, underscoring the ecological benefits of our approach.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453750","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
Anion-Relay Double Aza-Michael-Michael Cascades to Enone-Tethered Cyclohexadienones: Access to an Intricate Bridged Ring System.
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-26 DOI: 10.1021/acs.orglett.4c01009
Anil Chauhan, Raj Kumar Patel, Akhilesh Yadav, Ruchir Kant, Ravindra Kumar
{"title":"Anion-Relay Double Aza-Michael-Michael Cascades to Enone-Tethered Cyclohexadienones: Access to an Intricate Bridged Ring System.","authors":"Anil Chauhan, Raj Kumar Patel, Akhilesh Yadav, Ruchir Kant, Ravindra Kumar","doi":"10.1021/acs.orglett.4c01009","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01009","url":null,"abstract":"<p><p>An anion-relay double aza-Michael-Michael addition strategy has been reported for the synthesis of intricate scaffolds from enone-tethered cyclohexadienones and primary amines. This method discloses the base-catalyzed synthesis of highly valued bridged aza-tricyclic frameworks with a high level of product selectivity and stereoselectivity. Gram scale synthesis and synthetic transformation were shown to afford structurally diverse bridged aza-polycyclic amines. Control experiments and the kinetic profile were studied to determine a plausible reaction mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453748","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
Development of an Easy-To-Handle Redox Active Group for Alcohols: Catalytic Transformation of Tertiary Alcohols to Nitriles.
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-26 DOI: 10.1021/acs.orglett.4c01580
Seunghee Lee, Gyumin Kang, Sunkyu Han
{"title":"Development of an Easy-To-Handle Redox Active Group for Alcohols: Catalytic Transformation of Tertiary Alcohols to Nitriles.","authors":"Seunghee Lee, Gyumin Kang, Sunkyu Han","doi":"10.1021/acs.orglett.4c01580","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01580","url":null,"abstract":"<p><p>The generation of radical intermediates via SET-mediated deoxygenation of activated alcohol derivatives is desirable, as alcohols can be utilized in various radical-mediated reactions. Herein, we introduce α-<i>N</i>-phthalimido-oxy isobutyrate (NPIB) as a novel activating group for alcohols. Essentially, it is a more chemically robust alternative to Overman's <i>N</i>-phthalimidoyl oxalate group. The utility of the NPIB group is showcased in the conversion of tertiary alcohols to nitriles under Ir/Cu dual catalysts and in the presence of TMSCN upon blue LED irradiation. With our newly developed NPIB handle, the reactivities of <i>N</i>-hydroxyphthalimide esters derived from carboxylic acids would be achievable with naturally and commercially more abundant alcohol substrates.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453749","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
Balancing Reactivity, Regioselectivity, and Product Stability in Ir-Catalyzed Ortho-C-H Borylations of Anilines by Modulating the Diboron Partner. 通过调节二硼伙伴平衡 Ir 催化苯胺正交-C-H硼烷基化反应的反应性、区域选择性和产物稳定性。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-26 DOI: 10.1021/acs.orglett.4c01495
Jose R Montero Bastidas, Anshu Yadav, Seokjoo Lee, Behnaz Ghaffari, Milton R Smith, Robert E Maleczka
{"title":"Balancing Reactivity, Regioselectivity, and Product Stability in Ir-Catalyzed Ortho-C-H Borylations of Anilines by Modulating the Diboron Partner.","authors":"Jose R Montero Bastidas, Anshu Yadav, Seokjoo Lee, Behnaz Ghaffari, Milton R Smith, Robert E Maleczka","doi":"10.1021/acs.orglett.4c01495","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01495","url":null,"abstract":"<p><p>Ir-catalyzed arene C-H borylations (CHB) of anilines can be highly ortho selective by using a small B<sub>2</sub>eg<sub>2</sub> (eg = ethane-1,2-diol) as the borylating reagent. Unfortunately, the products are prone to decomposition, and transesterification with pinacol is required prior to isolation. This work offers a solution by adjusting the size of the diboron reagent. Based on our evaluation, we conclude that B<sub>2</sub>bg<sub>2</sub> (bg = butane-1,2-diol) achieves an optimal balance between CHB regioselectivity and stability for the borylated products.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141449103","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
Pd-Catalyzed Atroposelective C-H Olefination: Diverse Synthesis of Axially Chiral Biaryl-2-carboxylic Acids. Pd 催化的无选择性 C-H 烯化反应：轴向手性双芳基-2-羧酸的多样化合成。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-06-26 DOI: 10.1021/acs.orglett.4c01656
Ao-Lian Jiang, Gang Zhou, Bo-Yang Jiang, Tao Zhou, Xue-Tao Xu, Bing-Feng Shi
{"title":"Pd-Catalyzed Atroposelective C-H Olefination: Diverse Synthesis of Axially Chiral Biaryl-2-carboxylic Acids.","authors":"Ao-Lian Jiang, Gang Zhou, Bo-Yang Jiang, Tao Zhou, Xue-Tao Xu, Bing-Feng Shi","doi":"10.1021/acs.orglett.4c01656","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01656","url":null,"abstract":"<p><p>Axially chiral carboxylic acids are important motifs in chiral catalysts and ligands. We herein reported the synthesis of axially chiral carboxylic acids via Pd(II)-catalyzed atroposelective C-H olefination using carboxylic acid as the native directing group. A broad range of axial chiral biaryl-2-carboxylic acids were synthesized in good yields with high enantioselectivities (up to 84% yield with 99% ee). Gram-scale reaction and further transformation reactions also provide a platform for synthetic applications of this method.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453754","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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