The Journal of Organic Chemistry最新文献_第6页

Exceptions, Paradoxes, and Their Resolutions in Chemical Reactivity. 化学反应中的例外、悖论及其解决方案。

IF 3.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-06 DOI: 10.1021/acs.joc.4c02246

Guanqi Qiu

{"title":"Exceptions, Paradoxes, and Their Resolutions in Chemical Reactivity.","authors":"Guanqi Qiu","doi":"10.1021/acs.joc.4c02246","DOIUrl":"10.1021/acs.joc.4c02246","url":null,"abstract":"Progress in chemistry has primarily been framed through inductive processes, leading to the frequent emergence of exceptions and unexpected reactivities. These anomalies─ranging from surprising reactivity trends and paradoxical understandings to unanticipated parameter influences and unexpected successes or failures in synthetic methods─offer valuable insights that can drive scientific discovery. While it is commonly accepted that such exceptions can drive progress, many have been passively accepted without being explored for opportunities. Although numerous chemists have addressed exceptions and refined chemical models and theories, employing a systematic framework for actively exploring and understanding the underlying causes of exceptions could resolve paradoxes in broader contexts and create a greater impact than treating anomalies as isolated occurrences. This perspective demonstrates a proactive epistemic approach to uncovering the opportunities presented by exceptions and promotes deliberate, thoughtful engagement with paradoxes and anomalies. While the examples primarily focus on physical organic chemistry, the concepts are broadly applicable across various fields in chemical science. The thinking framework presented here is neither exhaustive nor prescriptive, but it outlines one of many potentially possible ways to inspire further development in how these anomalies could be harnessed for advancement.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16307-16316"},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142589557","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 : 2024-11-15 Epub Date: 2024-02-07 DOI: 10.1021/acs.joc.3c02348

Wen-Feng Li, Qing-Hao Xu, Qi-Yue Miao, Bin Xiao

引用次数: 0

[(NHC)Pd(OAc)₂]: Highly Active Carboxylate Pd(II)-NHC (NHC = N-Heterocyclic Carbene) Precatalysts for Suzuki-Miyaura and Buchwald-Hartwig Cross-Coupling of Amides by N-C(O) Activation. (NHC)Pd(OAc)2]：用于通过 N-C(O)活化酰胺的 Suzukii-Miyaura 和 Buchwald-Hartwig 交叉偶联的高活性羧酸盐 Pd(II)-NHC（NHC = N-杂环碳烯）前催化剂。

IF 4.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-07-01 DOI: 10.1021/acs.joc.4c00103

Yawei Zhu, Shiyi Yang, Tongliang Zhou, Michal Szostak

{"title":"[(NHC)Pd(OAc)2]: Highly Active Carboxylate Pd(II)-NHC (NHC = N-Heterocyclic Carbene) Precatalysts for Suzuki-Miyaura and Buchwald-Hartwig Cross-Coupling of Amides by N-C(O) Activation.","authors":"Yawei Zhu, Shiyi Yang, Tongliang Zhou, Michal Szostak","doi":"10.1021/acs.joc.4c00103","DOIUrl":"10.1021/acs.joc.4c00103","url":null,"abstract":"In the past eight years, the selective cross-coupling of amides by N-C(O) bond activation has emerged as a highly attractive manifold for the manipulation of traditionally unreactive amide bonds. In this Special Issue on Next-Generation Cross-Coupling Chemistry, we report the Suzuki-Miyaura and Buchwald-Hartwig cross-coupling of amides by selective N-C(O) cleavage catalyzed by bench-stable, well-defined carboxylate Pd(II)-NHC (NHC = N-heterocyclic carbene) catalysts {[(NHC)Pd(O2CR)2]}. This class of Pd(II)-NHCs promotes cross-coupling under exceedingly mild room-temperature conditions owing to the facile dissociation of the carboxylate ligands to form the active complex. These readily accessible Pd(II)-NHC precatalysts show excellent functional group tolerance and are compatible with a broad range of amide activating groups. Considering the mild conditions for the cross-coupling and the facile access to carboxylate Pd(II)-NHC complexes, we anticipate that this class of bench-stable complexes will find wide application in the activation of amide N-C(O) and related acyl X-C(O) bonds.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16203-16213"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141475449","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. 铜催化的 N,N-4-三苯基噻唑-2-胺的一锅合成。

IF 4.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-10-28 DOI: 10.1021/acs.joc.4c01417

Jia-Hao Weng, Xiao-Hu Xu, Zhi-Peng Guan, Zhi-Bing Dong

引用次数: 0

Discovery of A Synthetic Hub for Regio- and Stereoselective Construction of Triazolyl Vinyl Sulfonyl Fluorides. 发现三唑基乙烯基磺酰氟的区域和立体选择性合成枢纽。

IF 4.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-01 DOI: 10.1021/acs.joc.4c02186

Dengfeng Shu, Eman Fayad, Ola A Abu Ali, Hua-Li Qin

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 4.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-10-28 DOI: 10.1021/acs.joc.4c02001

Hong-Hai Zhang, Meng-Zhe Chen, Xinbin Yu, Peter V Bonnesen, Zili Wu, Hsin-Lung Chen, Hugh O'Neill

引用次数: 0

Correction to "TFA-Mediated DMSO-Participant Sequential Oxidation/1,3-Dipolar Cycloaddition Cascade of Pyridinium Ylides for the Assembly of Indolizines". 对 "TFA 介导的 DMSO 参与的吡啶鎓酰化物序贯氧化/1,3-二极环加成级联用于组装吲哚利嗪类化合物 "的更正。

IF 4.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-10-31 DOI: 10.1021/acs.joc.4c02552

Wen-Ming Shu, Jian-Xin He, Xun-Fang Zhang, Shuai Wang, An-Xin Wu

引用次数: 0

Synthesis of Indole- and Benzofuran-Based Benzylic Sulfones by Palladium-Catalyzed Sulfonylation of ortho-Iodoaryl Allenes. 通过钯催化邻碘芳基烯烃的磺酰化合成吲哚基和苯并呋喃基苄基砜。

IF 4.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-06 DOI: 10.1021/acs.joc.4c01953

Yuan Yin, Cangzhu Hu, Jing Sun, Kun Huang, Chao-Guo Yan, Lei Wang, Ying Han

引用次数: 0

Rhodium-Catalyzed Enantioselective Ring-Openings of Oxabicyclic Alkenes with Azole Nucleophiles. 铑催化的羰基双环烯与偶氮唑核亲和剂的对映选择性开环。

IF 4.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-11-06 DOI: 10.1021/acs.joc.4c02437

Matthew T Zambri, Armaan Grewal, Mark Lautens, Mark S Taylor

引用次数: 0

Iron-Catalyzed sp³ C-H Alkylation of Fluorene with Primary and Secondary Alcohols: A Borrowing Hydrogen Approach. 铁催化芴与伯醇和仲醇的 sp3 C-H 烷基化反应：一种借氢方法。

IF 4.3 2区化学

The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-08-23 DOI: 10.1021/acs.joc.4c00819

Ratnakar Saha, Bhairab Chand Hembram, Surajit Panda, Rahul Ghosh, Bidraha Bagh

{"title":"Iron-Catalyzed sp3 C-H Alkylation of Fluorene with Primary and Secondary Alcohols: A Borrowing Hydrogen Approach.","authors":"Ratnakar Saha, Bhairab Chand Hembram, Surajit Panda, Rahul Ghosh, Bidraha Bagh","doi":"10.1021/acs.joc.4c00819","DOIUrl":"10.1021/acs.joc.4c00819","url":null,"abstract":"The utilization of earth-abundant, cheap, and nontoxic transition metals in important catalytic transformations is essential for sustainable development, and iron has gained significant attention as the most abundant transition metal. A mixture of FeCl2 (3 mol %), phenanthroline (6 mol %), and KOtBu (0.4 eqivalent) was used as an effective catalyst for the sp3 C-H alkylation of fluorene using alcohol as a nonhazardous alkylating partner, and eco-friendly water was formed as the only byproduct. The substrate scope includes a wide range of substituted fluorenes and substituted benzyl alcohols. The reaction is equally effective with challenging secondary alcohols and unactivated aliphatic alcohols. Selective mono-C9-alkylation of fluorenes with alcohols yielded the corresponding products in good isolated yields. Various postfunctionalizations of C-9 alkylated fluorene products were performed to establish the practical utility of this catalytic alkylation. Control experiments suggested a homogeneous reaction path involving borrowing hydrogen mechanism with the formation and subsequent reduction of 9-alkylidene fluorene intermediate.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16223-16241"},"PeriodicalIF":4.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142034523","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