Solvent Dictated Organic Transformations.

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemistry - An Asian Journal Pub Date : 2024-11-07 DOI:10.1002/asia.202400603

Tamanna Khandelia, Pritishree Panigrahi, Subhendu Ghosh, Raju Mandal, Barlina Doley, Bhisma K Patel

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Abstract

Solvent plays an important role in many chemical reactions. The C-H activation has been one of the most powerful tools in organic synthesis. These reactions are often assisted by solvents which not only provide a medium for the chemical reactions but also facilitate reaching to the product stage. The solvent helps the reaction profile both chemically and energetically to reach the targeted product. Organic transformations via C-H activation from the solvent assistance perspective has been discussed in this review. Various solvents such as tetrahydrofuran (THF), MeCN, dichloromethane (DCM), dimethoxyethane (DME), 1,2-dichloroethane (1,2-DCE), dimethylformamide (DMF), dimethylsulfoxide (DMSO), isopropyl nitrile (ⁱPrCN), 1,4-dioxane, AcOH, trifluoroacetic acid (TFA), Ac₂O, PhCF₃, chloroform (CHCl₃), H₂O, N-methylpyrrolidone (NMP), acetone, methyl tert-butyl ether (MTBE), toluene, p-xylene, alcohols, MeOH, 1,1,1-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), tert-amyl alcohol and their roles are discussed. The exclusive role of the solvent in various transformations has been deliberated by highlighting the substrate scope, along with the proposed mechanisms. For easy classification, the review has been divided into three parts: (i) solvent-switched divergent C-H activation; (ii) C-H bond activation with solvent as the coupling reagent, and (iii) C-H activation with solvent caging and solvent-assisted electron donor acceptor (EDA) complex formation and autocatalysis.

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溶剂决定的有机转化。

溶剂在许多化学反应中都扮演着重要角色。C-H 活化是有机合成中最强大的工具之一。这些反应通常需要溶剂的辅助，溶剂不仅为化学反应提供了介质，还有助于反应进入产物阶段。溶剂可以从化学和能量两方面帮助反应曲线达到目标产物。本综述从溶剂辅助的角度讨论了通过 C-H 活化进行的有机转化。各种溶剂如四氢呋喃 (THF)、MeCN、二氯甲烷 (DCM)、二甲氧基乙烷 (DME)、1,2-二氯乙烷 (1,2-DCE)、二甲基甲酰胺 (DMF)、二甲基亚砜 (DMSO)、异丙基腈 (iPrCN)、1,4-二氧六环、AcOH、三氟乙酸 (TFA)、Ac2O、PhCF3、氯仿 (CHCl3)、H2O、N-甲基吡咯烷酮 (NMP)、丙酮、甲基叔丁基醚 (MTBE)、甲苯、对二甲苯、醇类、MeOH、1,1,1-三氟乙醇 (TFE)、1,1,1,3,3,3-六氟异丙醇 (HFIP)、叔戊醇及其作用。通过强调底物范围和拟议机制，讨论了溶剂在各种转化中的专属作用。为便于分类，综述分为三个部分：(i) 溶剂切换的发散 C-H 活化；(ii) 以溶剂为偶联试剂的 C-H 键活化；(iii) 以溶剂笼和溶剂辅助电子供体受体 (EDA) 复合物形成和自催化的 C-H 活化。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).