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Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene. 在α-蒎烯的每个可用碳原子上进行特定位点氘结合的策略和战术。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-22 DOI: 10.1021/acs.joc.4c01702
Jingyi Luo, Mary Alice Upshur, Marvin Vega, Nicolle A Doering, Jonathan Varelas, Zhouyang Ren, Franz M Geiger, Richmond Sarpong, Regan J Thomson
{"title":"Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene.","authors":"Jingyi Luo, Mary Alice Upshur, Marvin Vega, Nicolle A Doering, Jonathan Varelas, Zhouyang Ren, Franz M Geiger, Richmond Sarpong, Regan J Thomson","doi":"10.1021/acs.joc.4c01702","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01702","url":null,"abstract":"<p><p>The development of several unique strategies and tactics for the synthesis of α-pinene isotopologues that has culminated in access to all eight possible isomers with deuterium incorporated selectively at each available carbon atom is described. Access to this library of isotopologues provides new tools to more fully investigate the atmospheric autoxidation of α-pinene, a complex process that plays a major role in the formation of secondary organic aerosol in the Earth's atmosphere.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277367","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 Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective 分子内硅烷氧-迈克尔反应与附硝基烯：外消旋和对映体选择性
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-21 DOI: 10.1021/acs.joc.4c01625
Harshit Joshi, Shyam Sathyamoorthi
{"title":"Intramolecular Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective","authors":"Harshit Joshi, Shyam Sathyamoorthi","doi":"10.1021/acs.joc.4c01625","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01625","url":null,"abstract":"We present the first racemic and scalemic examples of di-<i>tert</i>-butyl silanoxy-Michael additions. Our operationally simple protocol is selective for nitro-olefins and simply involves stirring the substrate with an appropriate hydrogen-bond donor catalyst without any special precautions to exclude air or moisture. For each substrate examined, we have developed complementary protocols that optimize yield and enantioselectivity. Our reactions scale well, and the products are valuable intermediates for further transformations, including for the preparation of enantioenriched vicinal amino alcohols.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142273615","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
Chiral Binaphthol-Catalyzed Enantioselective Conjugate Addition of Alkenyl and Arylboronic Acids to α,β-Unsaturated Cyclic N-Sulfonyl Ketimines. 手性萘酚催化的烯基和芳基硼酸与 α、β-不饱和环 N-磺酰基酮亚胺的对映选择性共轭加成。
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.4c01269
Ya-Jing Hou, Yang-Ling Wang, Junbiao Chang, Guo-Li Chai
{"title":"Chiral Binaphthol-Catalyzed Enantioselective Conjugate Addition of Alkenyl and Arylboronic Acids to α,β-Unsaturated Cyclic <i>N</i>-Sulfonyl Ketimines.","authors":"Ya-Jing Hou, Yang-Ling Wang, Junbiao Chang, Guo-Li Chai","doi":"10.1021/acs.joc.4c01269","DOIUrl":"10.1021/acs.joc.4c01269","url":null,"abstract":"<p><p>The chiral binaphthol-catalyzed enantioselective conjugate addition of alkenylboronic acids and heteroarylboronic acids to cyclic <i>N</i>-sulfonyl ketimines is reported, providing the 1,4-addition products in high yields and moderate to excellent enantioselectivities (up to >99% ee). This mild, scalable catalytic system exhibits high efficiency and broad substrate scopes. Additionally, arylboronic acids were viable nucleophiles under more forcing 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":"142118367","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
Cascade Alkynyl Prins Cyclization and Aza-Michael Reaction: En Route to Regioselective Pyrano- and Isochromenoquinoline Scaffolds 级联炔烃 Prins 环化和 Aza-Michael 反应：获得区域选择性吡喃和异色喹啉支架的途径
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 DOI: 10.1021/acs.joc.4c01916
Subhamoy Biswas, Anil K. Saikia
{"title":"Cascade Alkynyl Prins Cyclization and Aza-Michael Reaction: En Route to Regioselective Pyrano- and Isochromenoquinoline Scaffolds","authors":"Subhamoy Biswas, Anil K. Saikia","doi":"10.1021/acs.joc.4c01916","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01916","url":null,"abstract":"A metal-free, Lewis acid approach for the regioselective synthesis of dihydropyranoquinoline scaffolds has been unveiled. The methodology employs a cascade alkynyl Prins–aza-Michael reaction sequence to deliver the products in good to excellent yields. The strategy features mild reaction conditions, broad substrate scope, and high functional group tolerance. The protocol has been further extended to include isochromenoquinoline derivatives. The utility of the reaction lies in the synthesis of highly fused polycyclic N,O-heterocycles via intramolecular Heck coupling. Additionally, a Rh(III)-catalyzed annulation results in the formation of highly fluorescent pentacyclic ammonium salts in excellent yields. Photophysical studies reveal that these pentacyclic ammonium salts exhibit strong emission in the green region (500–550 nm).","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":"142247226","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 Synthesis of Pharmaceutically Relevant Sulfonylureas via Direct Reaction of Sulfonamides with Amides. 通过磺酰胺与酰胺的直接反应无金属合成药用磺酰脲。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-08-28 DOI: 10.1021/acs.joc.4c01304
Sahil Mondal, Rakhi Sati, Muhammed Hashim, Rageshree Dash, Chandra Shekhar Nishad, Biplab Banerjee
{"title":"Metal-Free Synthesis of Pharmaceutically Relevant Sulfonylureas via Direct Reaction of Sulfonamides with Amides.","authors":"Sahil Mondal, Rakhi Sati, Muhammed Hashim, Rageshree Dash, Chandra Shekhar Nishad, Biplab Banerjee","doi":"10.1021/acs.joc.4c01304","DOIUrl":"10.1021/acs.joc.4c01304","url":null,"abstract":"<p><p>A metal-free process has been developed for the sustainable synthesis of medicinally important sulfonylureas in one pot via the direct reaction of sulfonamides with amides in green solvent (DMC). The reaction proceeded efficiently at room temperature, and the products were obtained in good to excellent yields. The use of readily accessible, inexpensive, and environmentally benign starting materials and reagents, metal-free mild reaction conditions, wide substrate scope, tolerance to air and moisture, operational simplicity, and good atom economy are the salient features of this reaction protocol. Gram-scale synthesis of antidiabetic drugs tolbutamide and chlorpropamide in excellent yields further revealed the practical utility of this procedure. Additionally, the synthetic value of this straightforward method is showcased by the late-stage modification of drug molecules, including drug-drug conjugation with good yields. Preliminary mechanistic studies indicated the <i>in situ</i> generation of an isocyanate intermediate, which further reacts with sulfonamide to form sulfonylurea. As compared to other related methods reported for sulfonylurea synthesis, the current method obviates the requirement of traditional multistep protocols involving isolation of hazardous isocyanates and avoids the use of toxic phosgene.</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":"142078432","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
Transition-Metal-Free Direct α-Arylation of Weinreb-type Amides with Arylboronic Acids through Aza-oxyallyl Cation Intermediates. 通过氮氧烯丙基阳离子中间体，用芳基硼酸对 Weinreb 型酰胺进行无过渡金属直接 α-芳基化。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-08-28 DOI: 10.1021/acs.joc.4c01391
Jiali Gao, Minmin Hu, Yuzhi Wang, Sanzhong Luo, Xueling Mi
{"title":"Transition-Metal-Free Direct α-Arylation of Weinreb-type Amides with Arylboronic Acids through Aza-oxyallyl Cation Intermediates.","authors":"Jiali Gao, Minmin Hu, Yuzhi Wang, Sanzhong Luo, Xueling Mi","doi":"10.1021/acs.joc.4c01391","DOIUrl":"10.1021/acs.joc.4c01391","url":null,"abstract":"<p><p>Here, we report an efficient transition-metal-free C(sp<sup>2</sup>)-C(sp<sup>3</sup>) Suzuki-Miyaura-type cross-coupling between α-halo Weinreb-type amides and arylboronic acids. The reaction is carried out by capturing active aza-oxyallyl cation (AOAC) with arylboronic acid to form a boron \"ate\" complex, followed by 1,4-migration to give α-aryl amides with good 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":"142078435","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
Direct α,β-C-H Difunctionalization of Piperidines for the Construction of the N,O-Acetal Skeleton via 1,5-Hydride Transfer. 通过 1,5-肼转移直接对哌啶进行 α,β-C-H-二官能化以构建 N,O-乙缩醛骨架。
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.4c01539
Yi Zhang, Jinqiang Kuang, Yongmin Ma, Lei Wang, Weiwei Fang
{"title":"Direct α,β-C-H Difunctionalization of Piperidines for the Construction of the <i>N</i>,<i>O</i>-Acetal Skeleton via 1,5-Hydride Transfer.","authors":"Yi Zhang, Jinqiang Kuang, Yongmin Ma, Lei Wang, Weiwei Fang","doi":"10.1021/acs.joc.4c01539","DOIUrl":"10.1021/acs.joc.4c01539","url":null,"abstract":"<p><p>Herein, we describe an unprecedented Lewis acid-catalyzed annulation of phenols with <i>o</i>-aminobenzaldehydes via a cascade coupling/1,5-hydride transfer/cyclization sequence. The α- and β-positions of cyclic amines were functionalized utilizing enamines generated <i>in situ</i>. A series of complex <i>N</i>,<i>O</i>-acetal derivatives are synthesized in moderate to good yields in one step. The methodology features high atom and step economy, excellent diastereoselectivity, and water as the sole byproduct.</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":"142138618","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
Phosphine-Catalyzed Crossed Rauhut-Currier-Type Coupling and [3 + 2]-Cycloaddition of 2-Alkylidene-3-oxindoles with Alkenes and Allenes to Access β,γ-Unsaturated Enones and Polycyclic Oxindoles. 磷催化 2-亚烷基-3-氧化吲哚与烯烃和醛的交叉 Rauhut-Currier 型偶联和 [3 + 2]- 环加成，以获得 β,γ-不饱和烯酮和多环氧化吲哚。
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.4c01402
Saikumar Banda, Lasse Johannßen, Alice Voss, Alexander Villinger, Gudrun Wenzel, Jens Holz, Malte Brasholz
{"title":"Phosphine-Catalyzed Crossed Rauhut-Currier-Type Coupling and [3 + 2]-Cycloaddition of 2-Alkylidene-3-oxindoles with Alkenes and Allenes to Access β,γ-Unsaturated Enones and Polycyclic Oxindoles.","authors":"Saikumar Banda, Lasse Johannßen, Alice Voss, Alexander Villinger, Gudrun Wenzel, Jens Holz, Malte Brasholz","doi":"10.1021/acs.joc.4c01402","DOIUrl":"10.1021/acs.joc.4c01402","url":null,"abstract":"<p><p>Dihydroazepino[1,2-<i>a</i>]indole diones are tricyclic <i>N</i>-acyl-2-alkylidene-3-oxindole enones that readily engage in tertiary phosphine-catalyzed intermolecular coupling reactions with acceptor-substituted alkenes. In these reactions, the tricyclic α-substituted enones undergo an α-alkylation with concomitant formation of a quaternary stereocenter, as well as the installation of a new double bond within the seven-membered azepane ring. The organocatalytic reaction constitutes a special case of the crossed intermolecular Rauhut-Currier reaction as the presence of the α-substituent in the enones prohibits the formation of an α,β-unsaturated product, but instead, skipped β,γ-unsaturated enones are obtained. With allene carboxylates as alternative coupling partners, the crossed Rauhut-Currier-type reaction competes with a regioselective allene to enone [3 + 2]-cycloaddition, and the product selectivity can be controlled by the choice of the phosphine organocatalyst.</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":"142138621","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
Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp3)-N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine. 布氏酸通过 N-烷基胺 C(sp3)-N 裂解引发 [6/7 + 1] 级联环化：苯并[1,4]氧氮杂环庚烷和二氢苯并[1,5]氧氮杂环辛的温和合成。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-01 DOI: 10.1021/acs.joc.4c01827
Lu Yin, Zhou Zhang, Shuntao Huang, Zhuoyu Wang, Chao Huang
{"title":"Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by <i>N</i>-Alkyl Amine C(sp<sup>3</sup>)-N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine.","authors":"Lu Yin, Zhou Zhang, Shuntao Huang, Zhuoyu Wang, Chao Huang","doi":"10.1021/acs.joc.4c01827","DOIUrl":"10.1021/acs.joc.4c01827","url":null,"abstract":"<p><p>A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides and <i>N</i>-alkyl amines. The substrate and acidic additives were employed to cleave the C(sp<sup>3</sup>)-N bond as a one-carbon synthon for C-C and C-O coupling, thus facilitating the [<i>n</i> + 1] cascade cyclization reaction, which enabled the construction of seven- and eight-membered <i>N</i>,<i>O</i>-heterocycles at room temperature. The method exhibits abroad substrate scope and remarkable tolerance toward various functional groups (seven-membered 28 examples, eight-membered 8 examples, and activated <i>N</i>-alkyl amine 12 examples) and utilization of natural products (2 examples).</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":"142102219","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(I)-Catalyzed Direct Addition of C(sp3)-H Bonds to Aryl Isocyanates. 锰（I）催化的 C（sp3）-H 键与芳基异氰酸酯的直接加成。
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.4c01581
Hongxin Liu, Zhichao Yu, Bin Li, Baiquan Wang
{"title":"Manganese(I)-Catalyzed Direct Addition of C(sp<sup>3</sup>)-H Bonds to Aryl Isocyanates.","authors":"Hongxin Liu, Zhichao Yu, Bin Li, Baiquan Wang","doi":"10.1021/acs.joc.4c01581","DOIUrl":"10.1021/acs.joc.4c01581","url":null,"abstract":"<p><p>The addition of C-H bonds to isocyanates catalyzed by transition metals is a highly auspicious methodology for providing synthetically and biologically important amides. However, the substrates are limited to C(sp<sup>2</sup>)-H bonds. In this work, an efficient manganese(I)-catalyzed direct addition reaction of C(sp<sup>3</sup>)-H bonds of 8-methylquinolines to aryl isocyanates has been developed, leading to the synthesis of various α-quinolinyl amide compounds in moderate to high yields. The reaction has a broad range of substrates and a good functional group tolerance. A possible mechanism is proposed based on the experimental results.</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":"142118368","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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