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Photocatalytic Defluorinative α-Aminoalkylation of Allylic Difluorides. 烯丙基二氟化物的光催化脱氟α-氨基烷基化反应。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-04 DOI: 10.1021/acs.joc.4c01861
Taylor Semeniuk, Ty Dudas, Esther Okeh, Tanner Felesky, Jean-Denys Hamel
{"title":"Photocatalytic Defluorinative α-Aminoalkylation of Allylic Difluorides.","authors":"Taylor Semeniuk, Ty Dudas, Esther Okeh, Tanner Felesky, Jean-Denys Hamel","doi":"10.1021/acs.joc.4c01861","DOIUrl":"10.1021/acs.joc.4c01861","url":null,"abstract":"<p><p>A photocatalytic process was devised to synthesize monofluoroalkenes via defluorinative functionalization of allylic difluorides. <i>N</i>-Alkylanilines are used as precursors to α-aminoalkyl radicals, which undergo regioselective addition to allylic difluorides, and subsequent SET and fluoride elimination produce monofluoroalkenes. C-C bond formation on the aniline is site-selective for the least substituted carbon α to nitrogen.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131202","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
Relative Rates of Transesterification vis-à-vis Newman's Rule of Six. 相对于纽曼 "六法则 "的酯交换率。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-06 DOI: 10.1021/acs.joc.4c01673
Arianna M H Wheeler, Sei-Chang Ahn, Niklas Kraemer, Thomas R Hoye
{"title":"Relative Rates of Transesterification vis-à-vis Newman's Rule of Six.","authors":"Arianna M H Wheeler, Sei-Chang Ahn, Niklas Kraemer, Thomas R Hoye","doi":"10.1021/acs.joc.4c01673","DOIUrl":"10.1021/acs.joc.4c01673","url":null,"abstract":"<p><p>The relative reactivity of a systematic series of simple aliphatic acetate esters has been measured. Exposure of pairs of esters of increasing remote steric hindrance (by altering the degree of branching of the ester alkyl group) to a methanolic solution of Cs<sub>2</sub>CO<sub>3</sub> proved to be a reliable (and general) method for quantitating the rate differences in these base-catalyzed transesterification reactions. The trends in relative rates are in accordance with the qualitative \"Rule of Six\" put forward by Melvin S. Newman in 1950, as deduced then from interpretation of earlier reports of ease of Fischer esterification reactions.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138623","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
Gold-Catalyzed Alkyne Oxidative Cyclization/Mannich-Type Addition Cascade Reaction of Ynamides with 1,3,5-Triazinanes. 金催化的炔烃氧化环化/1,3,5-三嗪酰胺的曼尼希式加成级联反应。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-05 DOI: 10.1021/acs.joc.4c01784
Kewei Chen, Chao Li, Shanliang Dong, Kemiao Hong, Jingjing Huang, Xinfang Xu
{"title":"Gold-Catalyzed Alkyne Oxidative Cyclization/Mannich-Type Addition Cascade Reaction of Ynamides with 1,3,5-Triazinanes.","authors":"Kewei Chen, Chao Li, Shanliang Dong, Kemiao Hong, Jingjing Huang, Xinfang Xu","doi":"10.1021/acs.joc.4c01784","DOIUrl":"10.1021/acs.joc.4c01784","url":null,"abstract":"<p><p>Herein, a gold-catalyzed alkyne oxidative cyclization/Mannich-type addition cascade reaction of ynamides with 1,3,5-triazinanes in the presence of a Brønsted acid has been presented. A class of functionalized fluorenes bearing a quaternary carbon center was synthesized directly with moderate to excellent yields via in situ formed α-oxo carbenes using quinoline <i>N</i>-oxide as the oxidant under mild reaction conditions.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138619","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
Ytterbium Triflate-Catalyzed Intramolecular Arylative Ring Opening of Arylaminomethyl-Substituted Donor–Acceptor Cyclopropanes: Access to Tetrahydroquinolines 三氟化硼镱催化的芳基氨基甲基取代的供体-受体环丙烷分子内芳基化开环：获得四氢喹啉
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 DOI: 10.1021/acs.joc.4c00924
Thangaraj Devaraj, Kannupal Srinivasan
{"title":"Ytterbium Triflate-Catalyzed Intramolecular Arylative Ring Opening of Arylaminomethyl-Substituted Donor–Acceptor Cyclopropanes: Access to Tetrahydroquinolines","authors":"Thangaraj Devaraj, Kannupal Srinivasan","doi":"10.1021/acs.joc.4c00924","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00924","url":null,"abstract":"The treatment of arylaminomethyl-substituted donor–acceptor cyclopropanes with a catalytic amount of Yb(OTf)<sub>3</sub> provides expedient access to tetrahydroquinoline derivatives. The transformation proceeds through an intramolecular S<sub>N</sub>2-type attack of the aminomethyl-containing aryl ring on the cyclopropane ring, leading to the formation of the products as single diastereomers.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142273612","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
Organic Bases as the Organic Electron Donors (OED) Promoted Reductive Coupling of Diarylhalomethanes: Halogens Controlled Construction of Tetraarylethylenes and Tetraarylethanes. 作为有机电子供体（OED）的有机碱促进二芳基卤代甲烷的还原偶联：卤素控制的四芳基乙烯和四芳基乙烷的构建。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-02 DOI: 10.1021/acs.joc.4c01219
Tong Li, Jie Mao, Shuwei Zhang, Qiyuan Ma, Yuqin Chen, Yu Yuan, Xiaodong Jia
{"title":"Organic Bases as the Organic Electron Donors (OED) Promoted Reductive Coupling of Diarylhalomethanes: Halogens Controlled Construction of Tetraarylethylenes and Tetraarylethanes.","authors":"Tong Li, Jie Mao, Shuwei Zhang, Qiyuan Ma, Yuqin Chen, Yu Yuan, Xiaodong Jia","doi":"10.1021/acs.joc.4c01219","DOIUrl":"10.1021/acs.joc.4c01219","url":null,"abstract":"<p><p>Using the organic base as the organic electron donors, the reductive coupling of diaryhalomethanes was smoothly achieved under transition-metal-free reaction conditions, giving a series of synthetically important tetraarylethylenes and tetraarylethanes in high yields. The mechanistic study revealed that the organic bases acting as the electron donor initiated the generation of a radical intermediate, realizing the construction of tetraarylethylene and tetraarylethane skeletons.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102220","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
Triplet Energy Transfer (EnT)-Promoted 1,3-Dipolar Cycloaddition Reactions of N-(Trimethylsilyl)methylphthalimide with Electron-Deficient Alkynes and Alkenes. 三重能量转移 (EnT) 促进的 N-(三甲基硅基)甲基邻苯二甲酰亚胺与缺电子炔和烯的 1,3-二极环加成反应。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-03 DOI: 10.1021/acs.joc.4c01287
Suk Hyun Lim, Hayeon You, Min-Ji Kim, Kyung-Ryang Wee, Dae Won Cho
{"title":"Triplet Energy Transfer (EnT)-Promoted 1,3-Dipolar Cycloaddition Reactions of <i>N</i>-(Trimethylsilyl)methylphthalimide with Electron-Deficient Alkynes and Alkenes.","authors":"Suk Hyun Lim, Hayeon You, Min-Ji Kim, Kyung-Ryang Wee, Dae Won Cho","doi":"10.1021/acs.joc.4c01287","DOIUrl":"10.1021/acs.joc.4c01287","url":null,"abstract":"<p><p>Triplet energy transfer (EnT)-promoted photochemical pathways, arisen by visible light and its photosensitizers, have gained significant attention as a complementary strategy for initiating organic transformations in photochemical reactions that are unlikely to occur through a single electron transfer (SET) process. In the present study, we investigated the triplet EnT-promoted 1,3-dipolar cycloaddition reactions of <i>N</i>-(trimethylsilyl)methylphthalimide with electron-deficient alkynyl and alkenyl dipolarophiles. The triplet excited state of <i>N</i>-(trimethylsilyl)methylphthalimide, promoted by the triplet EnT from thioxanthone (TXA) photosensitizer, underwent sequential intramolecular SET and carbon-to-oxygen migration of the silyl group to form azomethine ylide. This generated ylide cycloadded to alkynes or alkenes to regioselectively and stereospecifically produce a nitrogen-containing benzopyrrolizidine scaffold with multiple stereogenic centers. Crucially, the stereoselectivity of these cycloaddition reactions (i.e., endo versus exo addition) was influenced by the nature of the dipolarophiles.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118371","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
Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C-S Bond Activation. 通过 C-S 键活化实现苄基锍盐与硫代磺酸盐的交电偶联。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-03 DOI: 10.1021/acs.joc.4c01786
Xuan-Bo Hu, Yuwei Chen, Chen-Long Zhu, Hao Xu, Xiaocong Zhou, Weidong Rao, Xiao-Chun Hang, Xue-Qiang Chu, Zhi-Liang Shen
{"title":"Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C-S Bond Activation.","authors":"Xuan-Bo Hu, Yuwei Chen, Chen-Long Zhu, Hao Xu, Xiaocong Zhou, Weidong Rao, Xiao-Chun Hang, Xue-Qiang Chu, Zhi-Liang Shen","doi":"10.1021/acs.joc.4c01786","DOIUrl":"10.1021/acs.joc.4c01786","url":null,"abstract":"<p><p>A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142124215","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
NaOAc-Promoted [3+1+2] Annulation of O-Pivaloyl Oximes, Aldehydes, and 2-Methylbenzothiazole Salts: Synthesis of 1-Azaphenothiazines. NaOAc 促进 O-特戊酰基肟、醛和 2-甲基苯并噻唑盐的 [3+1+2] 嵌合：1-Azaphenothiazines 的合成。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-05 DOI: 10.1021/acs.joc.4c01590
Baihui Liang, Xiangya Cai, Shengting Xu, Jie Huang, Haiyin Deng, Weijie Ren, Jiehao Chen, Tsz Woon Benedict Lo, Xiuwen Chen, Zhongzhi Zhu
{"title":"NaOAc-Promoted [3+1+2] Annulation of <i>O</i>-Pivaloyl Oximes, Aldehydes, and 2-Methylbenzothiazole Salts: Synthesis of 1-Azaphenothiazines.","authors":"Baihui Liang, Xiangya Cai, Shengting Xu, Jie Huang, Haiyin Deng, Weijie Ren, Jiehao Chen, Tsz Woon Benedict Lo, Xiuwen Chen, Zhongzhi Zhu","doi":"10.1021/acs.joc.4c01590","DOIUrl":"10.1021/acs.joc.4c01590","url":null,"abstract":"<p><p>This paper presents an efficient strategy for constructing 1-azaphenothiazines through the NaOAc-promoted [3+1+2] annulation of <i>O</i>-pivaloyl oximes, aldehydes, and 2-methylbenzothiazole salts. The reaction is conducted in ethanol and employs oxygen as the oxidant under catalyst-free conditions. The process is amenable to various <i>O</i>-pivaloyl oximes, 2-methylbenzothiazole salts, and aldehydes, affording the target products in satisfactory yields.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131201","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
Microwave-Assisted Selective Nucleopalladation-Triggered Cascade Process: Synthesis of Highly Functionalized 3-Chloro-1H-indenes. 微波辅助的选择性核钯化触发级联过程：高功能化 3-氯-1H-茚的合成。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-04 DOI: 10.1021/acs.joc.4c01011
Tanvi Jandial, Anish Gupta, Dolma Tsering, Kamal K Kapoor, Vellaisamy Sridharan
{"title":"Microwave-Assisted Selective Nucleopalladation-Triggered Cascade Process: Synthesis of Highly Functionalized 3-Chloro-1<i>H</i>-indenes.","authors":"Tanvi Jandial, Anish Gupta, Dolma Tsering, Kamal K Kapoor, Vellaisamy Sridharan","doi":"10.1021/acs.joc.4c01011","DOIUrl":"10.1021/acs.joc.4c01011","url":null,"abstract":"<p><p>A nucleopalladation-triggered cascade transformation of internal alkynes bearing an amino nucleophile and an electrophilic enone was investigated under unconventional microwave-assisted conditions. Among the three possible pathways, the chloropalladation-triggered domino process proceeded selectively to furnish 3-chloro-1<i>H</i>-indenes in good to excellent yields. The reactions under microwave irradiation were completed in 30 min, and the conventional heating required 3-5 h for completion. The yields obtained under nonclassical heating using microwave irradiation are marginally higher (71-97%) than those of the conventional heating conditions (67-96%). The mechanism of this domino process involves chloropalladation of alkynes to deliver σ-vinylpalladium intermediates, intramolecular carbopalladation via Heck-type olefin insertion, and protodepalladation steps. The other two competitive intramolecular aminopalladation-initiated cascades via 7-<i>endo-dig</i> or 6-<i>exo-dig</i> cyclizations leading to oxazepine or benzoxazine scaffolds were not observed.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131200","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
Visible-Light-Driven Synthesis of Dihydroaurones from Aromatic Diazo Compounds. 利用可见光从芳香族重氮化合物合成二氢金牛酮。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-06 DOI: 10.1021/acs.joc.4c01064
Xiuyuan Duan, Guojun Zheng, Gang Xiao
{"title":"Visible-Light-Driven Synthesis of Dihydroaurones from Aromatic Diazo Compounds.","authors":"Xiuyuan Duan, Guojun Zheng, Gang Xiao","doi":"10.1021/acs.joc.4c01064","DOIUrl":"10.1021/acs.joc.4c01064","url":null,"abstract":"<p><p>Dihydroaurones, which are derivatives of aurones, exhibit similar biological activity. Although there are many synthetic methods for dihydroaurones, ecofriendly methodologies that circumvent the use of precious metals still need to be explored. In this work, a catalyst-free, visible-light-driven synthesis of dihydroaurones has been developed through the cyclization of aromatic diazo compounds. The reaction proceeded smoothly under mild conditions, resulting in a series of dihydroaurones in moderate to high yields. Mechanistic investigation suggests that this process involves a radical-pair Stevens rearrangement.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138626","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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