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机械化学傅-克酰基化反应

Mechanochemical Friedel-Crafts acylations.

作者信息

Đud Mateja, Briš Anamarija, Jušinski Iva, Gracin Davor, Margetić Davor

机构信息

Ruđer Bošković Institute, Bijenička cesta 54, HR-10002 Zagreb, Croatia.

出版信息

Beilstein J Org Chem. 2019 Jun 17;15:1313-1320. doi: 10.3762/bjoc.15.130. eCollection 2019.

DOI:10.3762/bjoc.15.130
PMID:31293680
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6604704/
Abstract

Friedel-Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.

摘要

傅克(FC)酰基化反应被用于制备酮官能化芳烃。开发了该具有工业重要性反应的更环保、无溶剂机械化学反应条件。研究了诸如傅克催化剂、时间、试剂比例和研磨载体等反应参数,以确定最佳反应条件。通过使用不同的芳烃与酸酐和酰化试剂结合来探索反应范围。结果表明,某些傅克反应活性芳烃可以在球磨条件下、无溶剂存在的情况下通过傅克酰基化有效地官能化。通过原位拉曼光谱和非原位红外光谱研究了反应机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/0a8a85b9e800/Beilstein_J_Org_Chem-15-1313-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/0c058b0bebe8/Beilstein_J_Org_Chem-15-1313-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/880a3bd56eb7/Beilstein_J_Org_Chem-15-1313-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/83496b2934ca/Beilstein_J_Org_Chem-15-1313-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/dafb8d1961be/Beilstein_J_Org_Chem-15-1313-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/94568b727372/Beilstein_J_Org_Chem-15-1313-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/6ab31d11673c/Beilstein_J_Org_Chem-15-1313-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/0a8a85b9e800/Beilstein_J_Org_Chem-15-1313-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/0c058b0bebe8/Beilstein_J_Org_Chem-15-1313-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/880a3bd56eb7/Beilstein_J_Org_Chem-15-1313-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/83496b2934ca/Beilstein_J_Org_Chem-15-1313-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/dafb8d1961be/Beilstein_J_Org_Chem-15-1313-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/94568b727372/Beilstein_J_Org_Chem-15-1313-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/6ab31d11673c/Beilstein_J_Org_Chem-15-1313-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/64e3/6604704/0a8a85b9e800/Beilstein_J_Org_Chem-15-1313-g002.jpg

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