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Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides 铁介导的烯丙基醚与苄基溴的二烷基化反应
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-04-04 DOI: 10.1021/acs.joc.3c0254810.1021/acs.joc.3c02548
Daniel M. Lux, Daniel J. Lee, Rishi R. Sapkota and Ramesh Giri*, 
{"title":"Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides","authors":"Daniel M. Lux,&nbsp;Daniel J. Lee,&nbsp;Rishi R. Sapkota and Ramesh Giri*,&nbsp;","doi":"10.1021/acs.joc.3c0254810.1021/acs.joc.3c02548","DOIUrl":"https://doi.org/10.1021/acs.joc.3c02548https://doi.org/10.1021/acs.joc.3c02548","url":null,"abstract":"<p >We disclose a method for the dibenzylation of alkenylarenes with benzyl bromides using iron powder. This reaction generates branched alkyl scaffolds adorned with functionalized aryl rings through the formation of two new C(sp<sup>3</sup>)–C(sp<sup>3</sup>) bonds at the vicinal carbons of alkenes. This protocol tolerates electron-rich, electron-neutral, and electron-poor benzyl bromides and alkenylarenes. Mechanistic studies suggest the formation of benzylic radical intermediates as a result of single-electron transfer from the iron, which is intercepted by alkenylarenes.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16292–16299 16292–16299"},"PeriodicalIF":3.3,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640641","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
Electrochemical Cross-Coupling between N-(4-Hydroxyphenyl)-sulfonamides and 2-Naphthols: Synthesis of 2,2′-Bis(arenol)s N-(4-羟基苯基)-磺酰胺与 2-萘酚的电化学交叉偶联：2,2′-双萘酚的合成
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-04-03 DOI: 10.1021/acs.joc.4c0002110.1021/acs.joc.4c00021
Zheng Zhu, Yanan Li*, Shitang Ma, Xuan Zhou, Yekai Huang, Jianan Sun* and Wei-Yi Ding*, 
{"title":"Electrochemical Cross-Coupling between N-(4-Hydroxyphenyl)-sulfonamides and 2-Naphthols: Synthesis of 2,2′-Bis(arenol)s","authors":"Zheng Zhu,&nbsp;Yanan Li*,&nbsp;Shitang Ma,&nbsp;Xuan Zhou,&nbsp;Yekai Huang,&nbsp;Jianan Sun* and Wei-Yi Ding*,&nbsp;","doi":"10.1021/acs.joc.4c0002110.1021/acs.joc.4c00021","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00021https://doi.org/10.1021/acs.joc.4c00021","url":null,"abstract":"<p >We herein present an electrochemical method for the dehydrogenative cross-coupling of <i>N</i>-(4-hydroxyphenyl)-sulfonamides and 2-naphthols. This transformation provides a direct and scalable approach to a wide range of <i>C</i><sub>1</sub>-symmetric 2,2′-bis(arenol)s with moderate to high yields under mild conditions. Preliminary attempts with the asymmetric variant of this reaction were also performed with ≤55% ee for the synthesis of 2,2′-bis(arenol)s. Control experiments were conducted to propose a plausible mechanism for the reaction.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16185–16194 16185–16194"},"PeriodicalIF":3.3,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640640","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
Rapid, Homogenous, B-Alkyl Suzuki–Miyaura Cross-Coupling of Boronic Esters 硼酸酯的快速、均质、B-烷基 Suzukii-Miyaura 交联反应
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-03-14 DOI: 10.1021/acs.joc.4c0008910.1021/acs.joc.4c00089
Matthew J. Bock,  and , Scott. E. Denmark*, 
{"title":"Rapid, Homogenous, B-Alkyl Suzuki–Miyaura Cross-Coupling of Boronic Esters","authors":"Matthew J. Bock,&nbsp; and ,&nbsp;Scott. E. Denmark*,&nbsp;","doi":"10.1021/acs.joc.4c0008910.1021/acs.joc.4c00089","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00089https://doi.org/10.1021/acs.joc.4c00089","url":null,"abstract":"<p >A rapid, anhydrous Suzuki–Miyaura cross-coupling of alkylboronic esters with aryl halides is described. Parallel experimentation revealed that the combination of AntPhos, an oxaphosphole ligand, neopentyldiol alkylboronic esters, and potassium trimethylsilanolate (TMSOK) enables successful cross-coupling. In general, reactions proceed in under 1 h with good yields and high linear/branched (<i>l</i>/<i>b</i>) selectivities. Crucially, two literature examples which previously took &gt;20 h to reach completion were accomplished in a fraction of the time with the method described herein. Mechanistic studies revealed that the reaction proceeds through a stereoretentive pathway and identified the boronic ester skeleton as a predominant pathway for deleterious protodehalogenation.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16195–16202 16195–16202"},"PeriodicalIF":3.3,"publicationDate":"2024-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640815","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
At the Speed of Light: The Systematic Implementation of Photoredox Cross-Coupling Reactions for Medicinal Chemistry Research 光速：在药物化学研究中系统实施光氧化交叉偶联反应
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-03-05 DOI: 10.1021/acs.joc.3c0235110.1021/acs.joc.3c02351
Nathan J. Gesmundo*, Alexander J. Rago, Jonathon M. Young, Sebastian Keess and Ying Wang*, 
{"title":"At the Speed of Light: The Systematic Implementation of Photoredox Cross-Coupling Reactions for Medicinal Chemistry Research","authors":"Nathan J. Gesmundo*,&nbsp;Alexander J. Rago,&nbsp;Jonathon M. Young,&nbsp;Sebastian Keess and Ying Wang*,&nbsp;","doi":"10.1021/acs.joc.3c0235110.1021/acs.joc.3c02351","DOIUrl":"https://doi.org/10.1021/acs.joc.3c02351https://doi.org/10.1021/acs.joc.3c02351","url":null,"abstract":"<p >The adoption of new and emerging techniques in organic synthesis is essential to promote innovation in drug discovery. In this Perspective, we detail the strategy we used for the systematic deployment of photoredox-mediated, metal-catalyzed cross-coupling reactions in AbbVie’s medicinal chemistry organization, focusing on topics such as assessment, evaluation, implementation, and accessibility. The comprehensive evaluation of photoredox reaction setups and published methods will be discussed, along with internal efforts to build expertise and photoredox high-throughput experimentation capabilities. We also highlight AbbVie’s academic–industry collaborations in this field that have been leveraged to develop new synthetic strategies, along with discussing the internal adoption of photoredox cross-coupling reactions. The work described herein has culminated in robust photocatalysis and cross-coupling capabilities which are viewed as key platforms for medicinal chemistry research at AbbVie.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16070–16092 16070–16092"},"PeriodicalIF":3.3,"publicationDate":"2024-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640816","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
Effects of Ring Size and Steric Encumbrance on Boron-to-Palladium Transmetalation from Arylboronic Esters 环尺寸和立体障碍对芳基硼酸酯硼钯反金属化的影响
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-02-29 DOI: 10.1021/acs.joc.3c0262910.1021/acs.joc.3c02629
Connor P. Delaney, Andrew F. Zahrt, Vincent M. Kassel and Scott E. Denmark*, 
{"title":"Effects of Ring Size and Steric Encumbrance on Boron-to-Palladium Transmetalation from Arylboronic Esters","authors":"Connor P. Delaney,&nbsp;Andrew F. Zahrt,&nbsp;Vincent M. Kassel and Scott E. Denmark*,&nbsp;","doi":"10.1021/acs.joc.3c0262910.1021/acs.joc.3c02629","DOIUrl":"https://doi.org/10.1021/acs.joc.3c02629https://doi.org/10.1021/acs.joc.3c02629","url":null,"abstract":"<p >The structure of the diol from which an arylboronic ester is derived dramatically influences the rate of transmetalation in the Suzuki-Miyaura cross-coupling reaction. Some esters undergo transmetalation more than 20 times faster than the parent arylboronic acid. Herein, investigations into the influence of arylboronic ester ring size and steric properties on the mechanism of transmetalation in the Suzuki-Miyaura reaction are described. Both factors impact the propensity of an arylboronic ester to bind to a dimeric palladium hydroxide complex. The reaction of hindered arylboronic esters derived from 1,2-diols (1,3,2-dioxaborolanes) with palladium hydroxide dimers to form a complex incorporating a Pd–O–B linkage is thermodynamically favorable, but the barrier to coordination is often higher than the barrier to arene transfer. In contrast, the analogous reaction between arylboronic esters derived from 1,3-diols (1,3,2-dioxaborinanes) and palladium hydroxide dimers is thermodynamically unfavorable, as 1,3,2-dioxaborinanes exhibit decreased electrophilicity compared to esters derived from 1,2- or 1,4-diols. These factors also influence the barrier of the arene transfer step, and in many cases, arylboronic esters that do not easily form Pd–O–B linked complexes undergo transmetalation faster than those that do because of hyperconjugative stabilization of the arene transfer transition state.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16170–16184 16170–16184"},"PeriodicalIF":3.3,"publicationDate":"2024-02-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640730","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 Electrochemical Iodination of 1-Arylpyridine N-Oxides 钯催化的 1-芳基吡啶 N-氧化物电化学碘化反应
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-02-27 DOI: 10.1021/acs.joc.3c0260110.1021/acs.joc.3c02601
Hang Zhou, Masahiro Miyasaka, Yu-Han Wang, Takuya Kochi and Fumitoshi Kakiuchi*, 
{"title":"Palladium-Catalyzed Electrochemical Iodination of 1-Arylpyridine N-Oxides","authors":"Hang Zhou,&nbsp;Masahiro Miyasaka,&nbsp;Yu-Han Wang,&nbsp;Takuya Kochi and Fumitoshi Kakiuchi*,&nbsp;","doi":"10.1021/acs.joc.3c0260110.1021/acs.joc.3c02601","DOIUrl":"https://doi.org/10.1021/acs.joc.3c02601https://doi.org/10.1021/acs.joc.3c02601","url":null,"abstract":"<p >The palladium-catalyzed C–H iodination of 1-arylpyridine <i>N</i>-oxides proceeded under electrochemical oxidation conditions using I<sub>2</sub> as an iodine source. The reaction of isoquinoline <i>N</i>-oxides possessing various <i>para</i>- or <i>meta</i>-substituted aryl groups at the 1-position proceeded to give the corresponding iodination products. Electron-donating groups on the aryl group facilitated the reaction to give relatively high yields of the product. The reaction was also found to be applicable to 2-aryl-3-picoline <i>N</i>-oxides.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16300–16306 16300–16306"},"PeriodicalIF":3.3,"publicationDate":"2024-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640729","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
Aryliodonium Salt-Induced Regioselective Access to meta-Substituted Anilines by Arylation of Azoles 芳基碘鎓盐通过芳基化偶氮类化合物诱导对元取代苯胺的区域选择性获取
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-02-22 DOI: 10.1021/acs.joc.3c0241710.1021/acs.joc.3c02417
Yaqi He, Yanan Li*, Xiangmei Ma, Xuan Zhou, Yekai Huang and Jianan Sun*, 
{"title":"Aryliodonium Salt-Induced Regioselective Access to meta-Substituted Anilines by Arylation of Azoles","authors":"Yaqi He,&nbsp;Yanan Li*,&nbsp;Xiangmei Ma,&nbsp;Xuan Zhou,&nbsp;Yekai Huang and Jianan Sun*,&nbsp;","doi":"10.1021/acs.joc.3c0241710.1021/acs.joc.3c02417","DOIUrl":"https://doi.org/10.1021/acs.joc.3c02417https://doi.org/10.1021/acs.joc.3c02417","url":null,"abstract":"<p >A highly efficient aryliodonium salt-induced regioselective access to <i>meta</i>-substituted anilines by arylation of azoles has been developed under catalyst-free conditions. This efficient transformation provides a facile and scalable approach to a wide range of biologically active <i>N</i>-arylazoles with moderate to high yields. According to the control experiments, two plausible pathways, including a Michael pathway and a free radical coupling pathway, for the reaction were proposed.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16282–16291 16282–16291"},"PeriodicalIF":3.3,"publicationDate":"2024-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640728","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 Chemoselective Phosphorylation of Poly(pseudo)halides: A Route for Organophosphorus Synthesis 钯催化多（假）卤化物的化学选择性磷酸化：有机磷合成路线
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-02-12 DOI: 10.1021/acs.joc.3c0234510.1021/acs.joc.3c02345
Zicong Chen, Wai Hang Pang, On Ying Yuen, Shan Shan Ng and Chau Ming So*, 
{"title":"Palladium-Catalyzed Chemoselective Phosphorylation of Poly(pseudo)halides: A Route for Organophosphorus Synthesis","authors":"Zicong Chen,&nbsp;Wai Hang Pang,&nbsp;On Ying Yuen,&nbsp;Shan Shan Ng and Chau Ming So*,&nbsp;","doi":"10.1021/acs.joc.3c0234510.1021/acs.joc.3c02345","DOIUrl":"https://doi.org/10.1021/acs.joc.3c02345https://doi.org/10.1021/acs.joc.3c02345","url":null,"abstract":"<p >We present an advancement in synthesizing organophosphorus compounds via chemoselective phosphorylation achieved by a palladium and SelectPhos ligand system (Pd/<b>L1</b>). This catalysis system exhibits remarkable chemoselectivity, even in poly(pseudo)halide substrates and overcoming toxicity and substrate scope limitations. The catalytic system is robust, which is demonstrated across diverse substrates such as chloroaryl and bromoaryl triflates. Furthermore, we present a one-pot sequential strategy combining phosphorylation with Suzuki–Miyaura coupling, providing a versatile platform for the efficient synthesis of complex organophosphorus compounds, challenging conventional reactivity paradigms.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16262–16268 16262–16268"},"PeriodicalIF":3.3,"publicationDate":"2024-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640727","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
Dual Nickel- and Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling To Access Chiral Secondary Benzylic Alcohols 镍和光氧化催化的不对称还原交叉偶联获得手性仲苄醇
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-02-07 DOI: 10.1021/acs.joc.3c0229310.1021/acs.joc.3c02293
Shun Wen, Jie Bu and Kun Shen*, 
{"title":"Dual Nickel- and Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling To Access Chiral Secondary Benzylic Alcohols","authors":"Shun Wen,&nbsp;Jie Bu and Kun Shen*,&nbsp;","doi":"10.1021/acs.joc.3c0229310.1021/acs.joc.3c02293","DOIUrl":"https://doi.org/10.1021/acs.joc.3c02293https://doi.org/10.1021/acs.joc.3c02293","url":null,"abstract":"<p >Transition-metal-catalyzed asymmetric cross-coupling represents a powerful strategy for C–C bond formation and the synthesis of enantiomerically pure molecules. Here, we report a dual nickel/photoredox-catalyzed enantioselective reductive cross-coupling of aryl halides with α-bromobenzoates, readily generated from aliphatic aldehydes, to provide diverse chiral secondary benzylic alcohols that are important motifs in bioactive natural products and pharmaceuticals. This dual catalytic system features mild conditions, good functional group tolerance, broad substrate scope, excellent enantiocontrol, and avoidance of stoichiometric metal reductants, presenting great potential for late-stage functionalization of complex molecules.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16134–16144 16134–16144"},"PeriodicalIF":3.3,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640731","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
Dual Photoredox/Nickel Catalysis Enables Diastereoselective Synthesis of Multisubstituted γ-Lactams Using Alkyl-GeMe3 as Radical Precursors 以烷基-GeMe3 为自由基前体，通过光氧化/镍双催化实现多取代γ-内酰胺的非对映选择性合成
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-02-07 DOI: 10.1021/acs.joc.3c0234810.1021/acs.joc.3c02348
Wen-Feng Li, Qing-Hao Xu, Qi-Yue Miao and Bin Xiao*, 
{"title":"Dual Photoredox/Nickel Catalysis Enables Diastereoselective Synthesis of Multisubstituted γ-Lactams Using Alkyl-GeMe3 as Radical Precursors","authors":"Wen-Feng Li,&nbsp;Qing-Hao Xu,&nbsp;Qi-Yue Miao and Bin Xiao*,&nbsp;","doi":"10.1021/acs.joc.3c0234810.1021/acs.joc.3c02348","DOIUrl":"https://doi.org/10.1021/acs.joc.3c02348https://doi.org/10.1021/acs.joc.3c02348","url":null,"abstract":"<p >Herein, we report a single-step, multicomponent approach to versatile γ-lactams through dual photoredox/nickel-catalyzed dicarbofunctionalization of α,β-unsaturated γ-butyrolactam. This reaction utilized alkyl trimethylgermanium as a radical precursor and acyl chloride as the electrophile, demonstrating remarkable functional group compatibility.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16269–16281 16269–16281"},"PeriodicalIF":3.3,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640732","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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