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Cs2CO3-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives 在 Cs2CO3 催化下合成 2,3-二氢苯并[b]氧杂卓衍生物的 Rauhut-Currier 型反应
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-29 DOI: 10.1021/acs.joc.4c0154410.1021/acs.joc.4c01544
Roger López, Omar Jamis-Oliva, Susan Lühr, Antonio Galdámez, Sebastián Gallardo-Fuentes* and Marcelo Vilches-Herrera*, 
{"title":"Cs2CO3-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives","authors":"Roger López,&nbsp;Omar Jamis-Oliva,&nbsp;Susan Lühr,&nbsp;Antonio Galdámez,&nbsp;Sebastián Gallardo-Fuentes* and Marcelo Vilches-Herrera*,&nbsp;","doi":"10.1021/acs.joc.4c0154410.1021/acs.joc.4c01544","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01544https://doi.org/10.1021/acs.joc.4c01544","url":null,"abstract":"<p >The synthesis of fused benzoxepines relies on the use of complex substrates and methodologies. Herein, we report our experimental and theoretical findings about an unprecedented Rauhut–Currier-type reaction catalyzed by Cs<sub>2</sub>CO<sub>3</sub> to access these important compounds. The developed methodology avoids the use of phosphine- or amine-based catalysts and additives. The reaction can be performed under microwave irradiation and proceeds with complete chemoselectivity.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16401–16405 16401–16405"},"PeriodicalIF":3.3,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641122","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
Diastereoselective Access to Ester-Substituted cis-Phenanthridinones via Hydrogen Atom Transfer-Involved 1,7-Enyne Bicyclization 通过氢原子转移参与的 1,7-乙炔双环化非对映选择性获得酯取代的顺式菲啶酮
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-29 DOI: 10.1021/acs.joc.4c0193710.1021/acs.joc.4c01937
Chuan Liu, Zonglang Wu, Guangpeng Yan, Chengyi Jiang, Min Dong, Shangyu Mao, Zhanwen Huang, Siping Wei, Dong Yi* and Yimou Gong*, 
{"title":"Diastereoselective Access to Ester-Substituted cis-Phenanthridinones via Hydrogen Atom Transfer-Involved 1,7-Enyne Bicyclization","authors":"Chuan Liu,&nbsp;Zonglang Wu,&nbsp;Guangpeng Yan,&nbsp;Chengyi Jiang,&nbsp;Min Dong,&nbsp;Shangyu Mao,&nbsp;Zhanwen Huang,&nbsp;Siping Wei,&nbsp;Dong Yi* and Yimou Gong*,&nbsp;","doi":"10.1021/acs.joc.4c0193710.1021/acs.joc.4c01937","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01937https://doi.org/10.1021/acs.joc.4c01937","url":null,"abstract":"<p >An organophotoredox-catalyzed 1,7-enyne bicyclization for the cis-diastereoselective synthesis of ester-substituted phenanthridinones has been achieved through radical cascade cyclization involving 1,6-hydrogen atom transfer. This transition-metal- and oxidant-free one-pot protocol generates three distinct C–C bonds and two quaternary carbon centers.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16632–16644 16632–16644"},"PeriodicalIF":3.3,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641083","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
Enantioselective Preparation of Cyclopentene-Based Amino Acids with a Quaternary Carbon Center 对映选择性制备具有季碳中心的环戊烯基氨基酸
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-29 DOI: 10.1021/acs.joc.4c0176410.1021/acs.joc.4c01764
Michael Franc, Pavel Měrka, Ivana Císařová and Jan Veselý*, 
{"title":"Enantioselective Preparation of Cyclopentene-Based Amino Acids with a Quaternary Carbon Center","authors":"Michael Franc,&nbsp;Pavel Měrka,&nbsp;Ivana Císařová and Jan Veselý*,&nbsp;","doi":"10.1021/acs.joc.4c0176410.1021/acs.joc.4c01764","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01764https://doi.org/10.1021/acs.joc.4c01764","url":null,"abstract":"<p >Azlactone is an important starting material for synthesizing amino acids containing a quaternary α-carbon. In this study, we have developed a sequential “one-pot” procedure involving an enantioselective spirocyclization reaction followed by acidic azlactone opening, which led to amino acid derivatives. The key step of this procedure is a spirocyclization between propargylated azlactones and enals by using a cooperative catalytic approach that combines chiral secondary amine and achiral Pd(0) complexes. The final acid opening of the azlactone motif allows isolation of the corresponding amino acid derivatives as major diastereoisomers in yields ranging from 37% to 70% with enantioselectivities of 85–97% ee. These synthesized amino acid derivatives hold great potential in the pharmaceutical and bioactive compound industries. Moreover, the final amino acid products with a cyclopentene moiety can be further derivatized, opening up even more possibilities for their application.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16522–16530 16522–16530"},"PeriodicalIF":3.3,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.joc.4c01764","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641082","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Switchable Divergent Electrochemical Hydrodehalogenation of gem-Dihalocyclopropanes gem-Dihalocyclopropanes 的可切换分歧电化学加氢脱卤反应
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-29 DOI: 10.1021/acs.joc.4c0174810.1021/acs.joc.4c01748
Jiayu Pan, Haoqi Qu, Yuanmeng Li, XiaoLi Bu, HongPing Deng, Hao Gong*, Mengtao Ma*, Li Xu* and Fei Xue*, 
{"title":"Switchable Divergent Electrochemical Hydrodehalogenation of gem-Dihalocyclopropanes","authors":"Jiayu Pan,&nbsp;Haoqi Qu,&nbsp;Yuanmeng Li,&nbsp;XiaoLi Bu,&nbsp;HongPing Deng,&nbsp;Hao Gong*,&nbsp;Mengtao Ma*,&nbsp;Li Xu* and Fei Xue*,&nbsp;","doi":"10.1021/acs.joc.4c0174810.1021/acs.joc.4c01748","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01748https://doi.org/10.1021/acs.joc.4c01748","url":null,"abstract":"<p >A comprehensive and effective electrochemical methodology is introduced for the diverse hydrodechlorination of <i>gem</i>-dichlorocyclopropanes and the ring cleavage hydrodefluorination of <i>gem</i>-difluorocyclopropanes under uniform electrochemical conditions. Moreover, the water content allows for the adjustable monohydrodechlorination or dihydrodechlorination of <i>gem</i>-dichlorocyclopropanes with exceptional chemoselectivity. Additionally, the mildness and practicality of this protocol facilitate its application to the late-stage functionalization of bioactive molecules. Mechanistic analyses suggest that the proton source may originate from acetonitrile.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16929–16935 16929–16935"},"PeriodicalIF":3.3,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641022","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
Metal-Free Oxidation of Acceptor–Donor Acylhydrazones into Diazo Compounds Using Phenyl Iododiacetate 使用碘代二乙酸苯酯将受体-供体酰肼无金属氧化成重氮化合物
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-29 DOI: 10.1021/acs.joc.4c0189310.1021/acs.joc.4c01893
Nour Tanbouza, Laurent Caron, Mojtaba Biniaz, Antony Marcoux and Thierry Ollevier*, 
{"title":"Metal-Free Oxidation of Acceptor–Donor Acylhydrazones into Diazo Compounds Using Phenyl Iododiacetate","authors":"Nour Tanbouza,&nbsp;Laurent Caron,&nbsp;Mojtaba Biniaz,&nbsp;Antony Marcoux and Thierry Ollevier*,&nbsp;","doi":"10.1021/acs.joc.4c0189310.1021/acs.joc.4c01893","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01893https://doi.org/10.1021/acs.joc.4c01893","url":null,"abstract":"<p >Aryl-ester acylhydrazones readily react with phenyl iododiacetate (PIDA) in methanol to produce the corresponding α-diazoesters with good to excellent yields (30 examples). The conditions have also been proven to be efficient in the synthesis of triazolopyridines. The crude mixture containing the diazo compound and acetic acid was also irradiated with low-energy blue LED light for a subsequent one-pot insertion of the in situ-generated carbene with AcOH to afford the respective acetates in high yields.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16600–16612 16600–16612"},"PeriodicalIF":3.3,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641084","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
Copper-Catalyzed One-Pot Synthesis of N,N-4-Triphenylthiazol-2-amines 铜催化单锅合成 N,N-4-三苯基噻唑-2-胺
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-28 DOI: 10.1021/acs.joc.4c0141710.1021/acs.joc.4c01417
Jia-Hao Weng, Xiao-Hu Xu, Zhi-Peng Guan* and Zhi-Bing Dong*, 
{"title":"Copper-Catalyzed One-Pot Synthesis of N,N-4-Triphenylthiazol-2-amines","authors":"Jia-Hao Weng,&nbsp;Xiao-Hu Xu,&nbsp;Zhi-Peng Guan* and Zhi-Bing Dong*,&nbsp;","doi":"10.1021/acs.joc.4c0141710.1021/acs.joc.4c01417","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01417https://doi.org/10.1021/acs.joc.4c01417","url":null,"abstract":"<p >Herein, we reported an efficient copper-catalyzed strategy for the synthesis of <i>N</i>,<i>N</i>-4-triphenylthiazol-2-amines from bromoacetophenone, phenylthiourea and iodobenzene. This method features good functional group tolerance, easy availability of starting materials and simplicity of operation, which provides an alternative method for the synthesis of 2-aminothiazoles.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16390–16400 16390–16400"},"PeriodicalIF":3.3,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641009","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
Correction to “Synthesis of Perdeuterated Alkyl Amines/Amides with Pt/C as Catalyst under Mild Conditions” 对 "在温和条件下以 Pt/C 为催化剂合成氚代烷基胺/酰胺 "的更正
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-28 DOI: 10.1021/acs.joc.4c0200110.1021/acs.joc.4c02001
Hong-Hai Zhang*, Meng-Zhe Chen, Xinbin Yu, Peter V. Bonnesen, Zili Wu, Hsin-Lung Chen and Hugh O’Neill, 
{"title":"Correction to “Synthesis of Perdeuterated Alkyl Amines/Amides with Pt/C as Catalyst under Mild Conditions”","authors":"Hong-Hai Zhang*,&nbsp;Meng-Zhe Chen,&nbsp;Xinbin Yu,&nbsp;Peter V. Bonnesen,&nbsp;Zili Wu,&nbsp;Hsin-Lung Chen and Hugh O’Neill,&nbsp;","doi":"10.1021/acs.joc.4c0200110.1021/acs.joc.4c02001","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02001https://doi.org/10.1021/acs.joc.4c02001","url":null,"abstract":"","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16975 16975"},"PeriodicalIF":3.3,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641014","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
Intramolecular/Intermolecular Sequential Cyclization Accompanied by Double C–F Bond Cleavage: Access to Tricyclic Fluorine-Containing Pyrano[3,2-c]chromenes 伴随双 C-F 键裂解的分子内/分子间顺序环化：获得含氟三环吡喃并[3,2-c]色烯
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-28 DOI: 10.1021/acs.joc.4c0185410.1021/acs.joc.4c01854
Dong-Sheng Yang, Xiang-Long Chen*, Chun-Yan Wu, You Zhou, Li-Sheng Wang, Yan-Dong Wu and An-Xin Wu*, 
{"title":"Intramolecular/Intermolecular Sequential Cyclization Accompanied by Double C–F Bond Cleavage: Access to Tricyclic Fluorine-Containing Pyrano[3,2-c]chromenes","authors":"Dong-Sheng Yang,&nbsp;Xiang-Long Chen*,&nbsp;Chun-Yan Wu,&nbsp;You Zhou,&nbsp;Li-Sheng Wang,&nbsp;Yan-Dong Wu and An-Xin Wu*,&nbsp;","doi":"10.1021/acs.joc.4c0185410.1021/acs.joc.4c01854","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01854https://doi.org/10.1021/acs.joc.4c01854","url":null,"abstract":"<p >Defluorinative cyclization of CF<sub>3</sub>-alkenes has emerged as a reliable strategy for crafting intricate polycyclic frameworks. In this study, a facile defluorinative bicyclization approach was developed for the construction of 4<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromenes under mild conditions involving a sequence of intramolecular cyclization and intermolecular defluoroheterocyclization. A variety of polysubstituted 4<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromenes featuring C2-fluorine could be synthesized in good yields with excellent tolerance toward various functional groups. Moreover, the introduction of a C–F bond provides additional possibilities for further modification of this skeleton. The product features aggregation-induced emission (AIE) characteristics after simple modification, which is promising for chemical and biomedical imaging.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16553–16563 16553–16563"},"PeriodicalIF":3.3,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640925","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
Palladium-Catalyzed Synthesis of Substituted Phenanthrenes via a C–H Annulation of 2-Biaryl Triflates with Alkynes 通过 2-Biaryl Triflates 与炔烃的 C-H 嵌合反应在钯催化下合成取代菲
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-28 DOI: 10.1021/acs.joc.4c0136910.1021/acs.joc.4c01369
Mohan Prabhakaran,  and , Kanniyappan Parthasarathy*, 
{"title":"Palladium-Catalyzed Synthesis of Substituted Phenanthrenes via a C–H Annulation of 2-Biaryl Triflates with Alkynes","authors":"Mohan Prabhakaran,&nbsp; and ,&nbsp;Kanniyappan Parthasarathy*,&nbsp;","doi":"10.1021/acs.joc.4c0136910.1021/acs.joc.4c01369","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01369https://doi.org/10.1021/acs.joc.4c01369","url":null,"abstract":"<p >A new palladium-catalyzed efficient method for the synthesis of substituted 9,10-phenanthrenes from 2-biaryl triflates with alkynes has been developed. This method provides a great opportunity to prepare various symmetrical and unsymmetrical phenanthrene derivatives in good yields. This reaction proceeds via C–OTf bond cleavage and alkyne insertion followed by C–H annulation.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16363–16374 16363–16374"},"PeriodicalIF":3.3,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641016","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 Synthesis of Enynals and Dihydrobenzo[f]isoquinolines via Deoxyalkynylation of Enaminones Enabled by the Cooperative Action of Tf2O/Pd/Cu 在 Tf2O/Pd/Cu 的协同作用下，通过烯氨酮的脱氧炔基合成烯氨酮和二氢苯并[f]异喹啉类化合物
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-27 DOI: 10.1021/acs.joc.4c0160310.1021/acs.joc.4c01603
Jianping Lin, Jiakai Tian, Yu Lu, Yiming Xu, Lulu Chen, Yucai Jiang, Mengping Guo, Xiaohan Zhang and Changyuan Zhang*, 
{"title":"Divergent Synthesis of Enynals and Dihydrobenzo[f]isoquinolines via Deoxyalkynylation of Enaminones Enabled by the Cooperative Action of Tf2O/Pd/Cu","authors":"Jianping Lin,&nbsp;Jiakai Tian,&nbsp;Yu Lu,&nbsp;Yiming Xu,&nbsp;Lulu Chen,&nbsp;Yucai Jiang,&nbsp;Mengping Guo,&nbsp;Xiaohan Zhang and Changyuan Zhang*,&nbsp;","doi":"10.1021/acs.joc.4c0160310.1021/acs.joc.4c01603","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01603https://doi.org/10.1021/acs.joc.4c01603","url":null,"abstract":"<p >A variety of enynals and dihydrobenzo[<i>f</i>]<i>iso</i>quinolines were effectively synthesized with favorable functional group compatibility via deoxyalkynylation of enaminones enabled by the cooperative action of Tf<sub>2</sub>O/Pd/Cu. The reaction system demonstrated the ability to be expanded to the deoxyarylation/deoxyaryloxylation of enaminones with arylboronic acids or phenols, facilitating the efficient formation of C–C/C–O bonds and showcasing the practicality and versatility of the methodology.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16419–16425 16419–16425"},"PeriodicalIF":3.3,"publicationDate":"2024-10-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640921","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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