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铁催化的碳-碳脱氢偶联反应：由醌/对苯二酚合成芳基醌

Iron catalyzed C-C dehydrogenative coupling reaction: synthesis of arylquinones from quinones/hydroquinones.

作者信息

Dong Yu, Xie Chun, Chen Jia, Shen Ai, Luo Qi-Qi, He Bing, Wang Zhi-Fan, Chang Bo, Yang Fan, Shi Zhi-Chuan

机构信息

College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University Chengdu 611130 P. R. China.

Southwest Minzu University Chengdu 610041 P. R. China.

出版信息

RSC Adv. 2022 Jan 28;12(6):3783-3787. doi: 10.1039/d1ra08828a. eCollection 2022 Jan 24.

DOI:10.1039/d1ra08828a
PMID:35425366
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8979275/
Abstract

An atom-economical approach for the synthesis of arylquinones was achieved successfully direct oxidative C-C dehydrogenative coupling reaction of quinones/hydroquinones with electron-rich arenes using an inexpensive Fe-I-(NH)SO system. The efficiency of this catalytic approach was established with a broad scope of substrates involving quinones and hydroquinones to give high yields (60-89%) of several arylated quinones. The present protocol is simple, practical, and shows good functional group tolerance.

摘要

通过使用廉价的Fe-I-(NH)SO体系，使醌/对苯二酚与富电子芳烃进行直接氧化C-C脱氢偶联反应，成功实现了一种原子经济的芳基醌合成方法。该催化方法的效率通过广泛的底物得以确立，这些底物包括醌和对苯二酚，能以60-89%的高产率得到多种芳基化醌。本方法简单、实用，且对官能团具有良好的耐受性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/827f/8979275/cb98add00a3b/d1ra08828a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/827f/8979275/895cbc7bb3b4/d1ra08828a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/827f/8979275/907e625c6a26/d1ra08828a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/827f/8979275/cb98add00a3b/d1ra08828a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/827f/8979275/895cbc7bb3b4/d1ra08828a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/827f/8979275/907e625c6a26/d1ra08828a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/827f/8979275/cb98add00a3b/d1ra08828a-s3.jpg

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本文引用的文献

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Catalytic Asymmetric Friedel-Crafts Alkylation of β,γ-Unsaturated α-Ketoesters: Enantioselective Addition of Aromatic C-H Bonds to Alkenes.β,γ-不饱和α-酮酯的催化不对称傅克烷基化反应：芳烃C-H键对烯烃的对映选择性加成
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Rh(III)-catalyzed direct C-H/C-H cross-coupling of quinones with arenes assisted by a directing group: identification of carbazole quinones as GSKβ inhibitors.导向基团辅助下铑（III）催化醌与芳烃的直接C-H/C-H交叉偶联反应：咔唑醌作为GSKβ抑制剂的鉴定
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Palladium-catalyzed direct C-H functionalization of benzoquinone.钯催化的对苯醌直接C-H官能团化反应
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