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Organophotoredox-Catalyzed Fluoroalkylation of Morita-Baylis-Hillman Adducts Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents. 以季氟烷基醇为氟烷基化试剂的有机光氧化还原催化森田-贝里斯-希尔曼加合物的氟烷基化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-15 DOI: 10.1021/acs.joc.5c01991
Wenchao Gao,Yong Teng,Qiang Zhao,Cunduo Tang,Xianchao Du,Wenguang Li,Xin Li,Ting Li
{"title":"Organophotoredox-Catalyzed Fluoroalkylation of Morita-Baylis-Hillman Adducts Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents.","authors":"Wenchao Gao,Yong Teng,Qiang Zhao,Cunduo Tang,Xianchao Du,Wenguang Li,Xin Li,Ting Li","doi":"10.1021/acs.joc.5c01991","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01991","url":null,"abstract":"Photoredox-enabled fluoroalkylation of MBH adducts using quaternary fluoroalkyl alcohols as the fluoroalkylating radical reagents is described. The facile protocol displays excellent functional group tolerance toward a series of synthetic allyl scaffolds containing fluoroalkyl groups under mild conditions. The alternative wavelength of visible light delivers the desired product with different yields and Z/E selectivities. A radical pathway involving an O-centered radical that induces β-scission to form the key fluoroalkyl radical is proposed in this transformation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288568","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
Cp*Co(III)-Catalyzed ortho-C-H Alkynylation of Pivalanilides with Bromoalkynes. Cp*Co(III)-催化Pivalanilides与溴炔的正碳氢炔化反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-15 DOI: 10.1021/acs.joc.5c02098
Yongqi Yu,Jiajia Yu,Mengdan You,Yanqi Li,Heyun Sheng,Rantao Huang,Wenguang Li,Ting Li
{"title":"Cp*Co(III)-Catalyzed ortho-C-H Alkynylation of Pivalanilides with Bromoalkynes.","authors":"Yongqi Yu,Jiajia Yu,Mengdan You,Yanqi Li,Heyun Sheng,Rantao Huang,Wenguang Li,Ting Li","doi":"10.1021/acs.joc.5c02098","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02098","url":null,"abstract":"A straightforward and efficient Cp*Co(III)-catalyzed ortho-C-H alkynylation of anilides with diverse readily available bromoalkynes was developed in which the weakly coordinating amide carbonyl group served as the directing group. This strategy provides a practical route for the synthesis of ortho-alkynylanilines, featuring good functional group tolerance and a broad substrate scope. Aryl-, alkyl-, and silyl-substituted bromoalkynes are compatible substrates in this catalytic system. Furthermore, subsequent synthetic transformations of the products demonstrate the synthetic utility of this methodology.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"37 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288490","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
Synthesis of Aryl and Alkyl Sulfonyl Cyanides Using KCN and NaOCl·5H2O in a Biphasic System. KCN和NaOCl·5H2O在双相体系中合成芳基和烷基磺酰氰化物。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-15 DOI: 10.1021/acs.joc.5c02290
Atsushi Baba,Yutaro Nakamura,Tsuyoshi Matsuzaki,Takeyuki Suzuki,Masaru Kondo,Ryo Takita
{"title":"Synthesis of Aryl and Alkyl Sulfonyl Cyanides Using KCN and NaOCl·5H2O in a Biphasic System.","authors":"Atsushi Baba,Yutaro Nakamura,Tsuyoshi Matsuzaki,Takeyuki Suzuki,Masaru Kondo,Ryo Takita","doi":"10.1021/acs.joc.5c02290","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02290","url":null,"abstract":"An efficient and practical protocol has been developed for synthesizing aryl and alkyl sulfonyl cyanides (R-SO2CN) from sodium sulfinates (R-SO2Na) by employing potassium cyanide (KCN) and sodium hypochlorite pentahydrate (NaOCl·5H2O) under weakly acidic conditions. A biphasic medium is essential for suppressing side reactions and enabling broad generality including 13C-labeled derivatives. In situ-generated cyanogen chloride (ClCN) was identified experimentally as the key reactive species. The synthetic utility is showcased through the enhanced reactivity of electronically tuned sulfonyl cyanides in useful transformations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288578","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
Manganese-Catalyzed Oxazoline-Directed C-H Addition of Arenes to Unsaturated Polar Bond: Experimental and Computational Study. 锰催化恶唑啉定向碳氢加成芳烃至不饱和极性键：实验与计算研究。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-15 DOI: 10.1021/acs.joc.5c01326
Ramiro Robles-Henríquez,Omar Jamis-Oliva,Tomás Chávez-Vega,Susan Lühr,Andrés F Flor-López,Tamara Maldonado,Sebastián Gallardo-Fuentes,Marcelo Vilches-Herrera
{"title":"Manganese-Catalyzed Oxazoline-Directed C-H Addition of Arenes to Unsaturated Polar Bond: Experimental and Computational Study.","authors":"Ramiro Robles-Henríquez,Omar Jamis-Oliva,Tomás Chávez-Vega,Susan Lühr,Andrés F Flor-López,Tamara Maldonado,Sebastián Gallardo-Fuentes,Marcelo Vilches-Herrera","doi":"10.1021/acs.joc.5c01326","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01326","url":null,"abstract":"The direct C-H aromatic addition to unsaturated polar bonds using abundant metals such as Mn and Co is scarce, and it has been mainly limited to the use of pyridine as a directing group. In this work, we introduce for the first time the use of oxazoline as a more versatile motif for this transformation, which can be further derivatized in other functional groups. The proposed mechanism shows a base-assisted formation of an Mn-tricarbonyl as the active species in the catalytic cycle, in contrast to the most reported Mn-tetracarbonyl complex. The mechanism was validated by experimental and DFT studies.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288525","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
Total Synthesis of Panaxydiol and (-)-Virol C. Panaxydiol和(-)- virol C的全合成。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-14 DOI: 10.1021/acs.joc.5c02020
Brian K Osei-Badu,Justin T Mohr
{"title":"Total Synthesis of Panaxydiol and (-)-Virol C.","authors":"Brian K Osei-Badu,Justin T Mohr","doi":"10.1021/acs.joc.5c02020","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02020","url":null,"abstract":"A direct approach to the total synthesis of panaxydiol (1) and (-)-virol C (2) is reported. This strategy highlights the utility of γ-polyhaloalkylation reactions of siloxydienes in target-directed synthesis, enabling the construction of functionalized conjugated π-systems poised for further manipulation. Titanium-mediated enantioselective transformations enable asymmetric synthesis and identify an unexpected discrepancy in facial selectivity that is resolved by total synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"32 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288579","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
Ir-f-Amphbinol-Catalyzed Asymmetric Hydrogenation of N-Protected α-Amino Ketones Followed by Deprotection for Preparation of β-Primary Amino Alcohols. ir -f-两性酚催化n保护α-氨基酮的不对称加氢和脱保护制备β-伯胺醇。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-14 DOI: 10.1021/acs.joc.5c01927
Weilong Wu,Wanyang Chen,Wenzhi Mo,Ning Qiu,Yueru Hao,Xiaolei Ge,Feng Zhang,Bingqing Liu,Dongsheng Deng,Yan Zhou,Baoming Ji
{"title":"Ir-f-Amphbinol-Catalyzed Asymmetric Hydrogenation of N-Protected α-Amino Ketones Followed by Deprotection for Preparation of β-Primary Amino Alcohols.","authors":"Weilong Wu,Wanyang Chen,Wenzhi Mo,Ning Qiu,Yueru Hao,Xiaolei Ge,Feng Zhang,Bingqing Liu,Dongsheng Deng,Yan Zhou,Baoming Ji","doi":"10.1021/acs.joc.5c01927","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01927","url":null,"abstract":"We have successfully developed a highly efficient Ir-f-Amphbinol-catalyzed asymmetric hydrogenation for various α-amino ketones with different substituents on the -NH2. A series of α-amino ketones containing easily introduced and removed groups (Boc-, Ac-, Bz-, Ts-) were successfully converted into the corresponding chiral alcohols with 96∼>99% yields, 95:5-97:3 dr, and 90∼>99% ee. The versatility of this method is demonstrated through the derivatization of products, including deprotection to get the key intermediates of six pharmaceuticals. Noteworthily, we have innovatively applied the chiral β-primary amino alcohol 3-1 prepared by the abovementioned method to the efficient synthesis of dominant chiral tridentate PNO-type ligands L1-L2 and applied them to the efficient iridium-catalyzed asymmetric hydrogenation of various ketones. Based on the literature reports and our experimental results, we further proposed a possible ONa/MH instead of NNa/MH bifunctional mechanism.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"171 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288572","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
[3 + 2] Annulation of Donor-Acceptor Cyclopropanes with Ammonium Thiocyanate: Interrupted Cascade Leads to Elusive Iminodihydrothiophene Derivatives. [3 + 2]给受体环丙烷与硫氰酸铵的环化：中断级联导致难以捉摸的亚氨基二氢噻吩衍生物。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-14 DOI: 10.1021/acs.joc.5c01986
Soumyadeep Roy Chowdhury,Deepak Singh,Apurba Samanta,Soumitra Maity
{"title":"[3 + 2] Annulation of Donor-Acceptor Cyclopropanes with Ammonium Thiocyanate: Interrupted Cascade Leads to Elusive Iminodihydrothiophene Derivatives.","authors":"Soumyadeep Roy Chowdhury,Deepak Singh,Apurba Samanta,Soumitra Maity","doi":"10.1021/acs.joc.5c01986","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01986","url":null,"abstract":"A zinc iodide-mediated [3 + 2] cyclization between donor-acceptor cyclopropanes and ammonium thiocyanate has been developed to afford 2-imino-tetrahydrothiophene derivatives under mild conditions. Subsequent transformation of these intermediates into 2-amino-dihydrothiophenes was achieved using neutral alumina as a Lewis acid. Unlike most of the previous methods that directly yield 2-amino-dihydrothiophenes, this approach enables selective access to unsubstituted 2-imino-tetrahydrothiophenes─a challenging target that is not widely accessible. This metal-mediated protocol is operationally simple, cost-effective, and environmentally benign. The synthetic utility of the products was demonstrated through a series of transformations, and a plausible reaction mechanism is proposed.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"117 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145284016","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
Electroreductive Homo-coupling of Quinolines for the Regioselective Synthesis of 1,2,3,4-Tetrahydro-2,3'-biquinolines. 喹啉类电还原均偶联在区域选择性合成1,2,3,4-四氢-2,3'-双喹啉中的应用。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-14 DOI: 10.1021/acs.joc.5c02225
Jie Xia,Yumei Li,Xiangyuan Yao,Fuhong Xiao,Guo-Jun Deng
{"title":"Electroreductive Homo-coupling of Quinolines for the Regioselective Synthesis of 1,2,3,4-Tetrahydro-2,3'-biquinolines.","authors":"Jie Xia,Yumei Li,Xiangyuan Yao,Fuhong Xiao,Guo-Jun Deng","doi":"10.1021/acs.joc.5c02225","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02225","url":null,"abstract":"A simple and efficient electrochemical reductive homocoupling strategy for the synthesis of 1,2,3,4-tetrahydro-2,3'-biquinoline from commercially available quinolines has been developed. This method employs diethyl phosphite and water as hydrogen sources. Mechanistic studies indicate that the regioselective C2-C3 coupling in this reaction proceeds via enamine-iminium intermediates. This sustainable approach combines good regioselectivity with broad functional group tolerance under mild conditions, while the modular biquinoline products serve as versatile scaffolds for late-stage functionalization and synthetic diversification.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288573","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
Divergent [4+3] Annulations of β'-Acetoxy Allenoates: Access to Azepino[1,2-a]indole Derivatives. β′-乙酰氧基Allenoates的发散[4+3]环：Azepino[1,2-a]吲哚衍生物的获取。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-14 DOI: 10.1021/acs.joc.5c01904
Yannan Zhu,You Huang
{"title":"Divergent [4+3] Annulations of β'-Acetoxy Allenoates: Access to Azepino[1,2-a]indole Derivatives.","authors":"Yannan Zhu,You Huang","doi":"10.1021/acs.joc.5c01904","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01904","url":null,"abstract":"In this work, the Lewis base-catalyzed divergent [4 + 3] annulation reactions of β'-acetoxy allenoates with two different indole derivatives are reported. A wide range of azepino[1,2-a]indole derivatives was smoothly obtained from 2-((3-formyl-1H-indol-2-yl)methyl)malonates by employing the DABCO catalyst. The syntheses of two regioselective diazepino[1,2-a]indole derivatives from 3-formyl-1H-indole-2-carboxamides are realized by the catalysis of DABCO and organophosphine, respectively. A series of functional group transformations can be achieved in the three 1,2-fused seven-membered indole products.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288492","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
Superelectrophilic Cyclizations Involving 2-Norbornyl Dications. 涉及2-降冰片适应症的超亲电环化。
IF 3.6 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-13 DOI: 10.1021/acs.joc.5c01982
Grant P Holmin, Milan Gembicky, Douglas A Klumpp
{"title":"Superelectrophilic Cyclizations Involving 2-Norbornyl Dications.","authors":"Grant P Holmin, Milan Gembicky, Douglas A Klumpp","doi":"10.1021/acs.joc.5c01982","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01982","url":null,"abstract":"<p><p>A series of anilino 2-norbornyl alcohols have been prepared and reacted in strongly acidic media. The chemistry provides ring-fused norbornane products in good yields (12 examples, 81-99% yields). A mechanism is proposed involving a novel ammonium-carbonium dicationic intermediate.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.6,"publicationDate":"2025-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145285030","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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