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以氟化醇作为氢键供体和溶剂的傅克烷基化反应。

Friedel-Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents.

作者信息

Tang Ren-Jin, Milcent Thierry, Crousse Benoit

机构信息

Faculty of Pharmacy, UMR 8076, BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay 92290 Châtenay-Malabry France

出版信息

RSC Adv. 2018 Mar 13;8(19):10314-10317. doi: 10.1039/c8ra01397g.

DOI:10.1039/c8ra01397g
PMID:35540471
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9078892/
Abstract

An effective and clean FC alkylation of indoles and electron-rich arenes with β-nitroalkenes in HFIP was reported. The desired products are formed rapidly in excellent yields under mild conditions without the need for any additional catalysts or reagents. Further, this methodology can be applied to one-pot synthesis of biologically active tryptamine derivatives.

摘要

据报道,在六氟异丙醇(HFIP)中,吲哚和富电子芳烃与β-硝基烯烃发生了有效且清洁的傅-克烷基化反应。在温和条件下,无需任何额外的催化剂或试剂,就能迅速以优异的产率形成所需产物。此外,该方法可应用于生物活性色胺衍生物的一锅法合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d376/9078892/5b79b73dff9c/c8ra01397g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d376/9078892/8469b0c2ecd2/c8ra01397g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d376/9078892/5caaf80c0692/c8ra01397g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d376/9078892/5b79b73dff9c/c8ra01397g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d376/9078892/8469b0c2ecd2/c8ra01397g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d376/9078892/5caaf80c0692/c8ra01397g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d376/9078892/5b79b73dff9c/c8ra01397g-s3.jpg

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本文引用的文献

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J Org Chem. 2018 Jan 19;83(2):930-938. doi: 10.1021/acs.joc.7b02920. Epub 2018 Jan 2.
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Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction.六氟-2-丙醇促进的分子间傅克酰基化反应。
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Fluorinated Alcohols as Activators for the Solvent-Free Chemical Fixation of Carbon Dioxide into Epoxides.氟化醇作为将二氧化碳无溶剂化学固定为环氧化物的活化剂。
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A database of dispersion-induction DI, electrostatic ES, and hydrogen bonding α1 and β1 solvent parameters and some applications to the multiparameter correlation analysis of solvent effects.一个包含色散诱导(DI)、静电(ES)以及氢键α1和β1溶剂参数的数据库及其在溶剂效应多参数相关分析中的一些应用。
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Friedel-Crafts reaction of benzyl fluorides: selective activation of C-F bonds as enabled by hydrogen bonding.弗里德尔-克拉夫茨反应的苄基氟化物:氢键使 C-F 键选择性活化。
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Solvatomagnetic Comparison Method: A Proper Quantification of Solvent Hydrogen-Bond Basicity.
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