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铜催化的多环芳烃(PAHs)远程C-H芳基化反应

Copper-catalyzed remote C-H arylation of polycyclic aromatic hydrocarbons (PAHs).

作者信息

Luo Anping, Zhang Min, Fu Zhangyi, Lan Jingbo, Wu Di, You Jingsong

机构信息

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P.R. China.

出版信息

Beilstein J Org Chem. 2020 Mar 30;16:530-536. doi: 10.3762/bjoc.16.49. eCollection 2020.

DOI:10.3762/bjoc.16.49
PMID:32280382
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7136547/
Abstract

The regioselective C-H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) is a desired but challenging task. A copper-catalyzed C7-H arylation of 1-naphthamides has been developed by using aryliodonium salts as arylating reagents. This protocol does not need to use precious metal catalysts and tolerates wide variety of functional groups. Under standard conditions, the remote C-H arylation of other PAHs including phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3-carboxamide has also accomplished, which provides an opportunity for the development of diverse organic optoelectronic materials.

摘要

取代多环芳烃(PAHs)的区域选择性C-H芳基化是一项令人期待但具有挑战性的任务。通过使用芳基碘鎓盐作为芳基化试剂,已开发出一种铜催化的1-萘酰胺的C7-H芳基化反应。该方法无需使用贵金属催化剂,并且能耐受多种官能团。在标准条件下,还实现了包括菲-9-甲酰胺、芘-1-甲酰胺和荧蒽-3-甲酰胺在内的其他多环芳烃的远程C-H芳基化反应,这为开发多种有机光电材料提供了契机。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/d48c9231d64b/Beilstein_J_Org_Chem-16-530-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/803911c79a3f/Beilstein_J_Org_Chem-16-530-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/82a70c417e88/Beilstein_J_Org_Chem-16-530-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/b920d1153561/Beilstein_J_Org_Chem-16-530-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/f78a62911a0f/Beilstein_J_Org_Chem-16-530-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/d48c9231d64b/Beilstein_J_Org_Chem-16-530-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/803911c79a3f/Beilstein_J_Org_Chem-16-530-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/82a70c417e88/Beilstein_J_Org_Chem-16-530-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/b920d1153561/Beilstein_J_Org_Chem-16-530-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/f78a62911a0f/Beilstein_J_Org_Chem-16-530-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c069/7136547/d48c9231d64b/Beilstein_J_Org_Chem-16-530-g002.jpg

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