可见光诱导下喹喔啉酮与吡咯衍生物的氧化偶联

doi:10.6023/cjoc202207031

摘要/Abstract

发展了一种区域选择性的喹喔啉酮3-位氧化偶联富电子吡咯衍生物的方法. 以$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$(3 mol%)为光敏剂, 空气氧为氧化剂, 高收率得到喹喔酮与吡咯衍生物的氧化偶联产物. 该方法底物的官能团适用范围广, 反应高效绿色, 可快速构建基于喹喔啉酮-吡咯衍生物的药物分子库. 相同测试条件下的Stern-Volmer荧光淬灭实验表明, 缺电子芳烃1-甲基喹喔啉酮对光敏剂的淬灭速率常数K_q=1.2×10⁹ L•mol^-1•s^-1, 而富电子芳烃1-甲基吡咯/1-甲基吲哚的淬灭常数约为1.06~1.07×10¹⁰ L•mol^-1•s^-1, 后者的荧光淬灭速率几乎是前者的10倍.

关键词: 氧化偶联, 喹喔啉酮, 光催化, 区域选择性

Herein, one feasible methodology has been developed for oxidative cross-coupling between quinoxalinones and electron-rich aromatic rings (pyrroles or indoles). Utilizing the commerial available photocatalyst $\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$ (3 mol%) as catalyst and air as external oxidant, the oxidative coupling products of quinolones and pyrrole derivatives were obtained in high yields. The protocol provides effective acceess to such quinoxalinones-pyrrole derivatives with profiles of broad functional group, efficient conversion and easy-handling. Furthermore, Stern-Volmer fluorescent quenching experiments under the same condition disclosed that quenching rate constant of electron-rich aromatic ring (pyrrole or indole, k_q 1.06×10¹⁰~1.07×10¹⁰ L•mol^-1•s^-1) was nearly one order of magnitude larger than that of electro-deficient quinoxalinones (k_q=1.2×10⁹ L•mol^-1•s^-1).

Key words: oxidative cross-coupling reaction, quinoxalinone, photocatalysis, regio-selectivity

引用此文

沈梦涵, 李来强, 周泉, 王洁慧, 王磊. 可见光诱导下喹喔啉酮与吡咯衍生物的氧化偶联[J]. 有机化学, 2023, 43(2): 697-704.

Menghan Shen, Laiqiang Li, Quan Zhou, Jiehui Wang, Lei Wang. Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 697-704.

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Entry	Photocatalyst	Light source/nm	Solvent	Yield^b/%
1	TPT	450~455	DCE	48
2	Mes-Acr-Me⁺ClO₄^‒	450~455	DCE	75
3	Ru(bpy)₃Cl₂	420~425	DCE	0
4	4CzIPN	420~425	DCE	0
5	Eosin Y	530~535	DCE	58
6	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	THF	12
7	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	Acetone	15
8	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	MeCN	11
9	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	DMSO	5
10	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	-	DCE	0^c
11	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	DCE	0^d

Entry	Photocatalyst	Light source/nm	Solvent	Yield^b/%
1	TPT	450~455	DCE	48
2	Mes-Acr-Me⁺ClO₄^‒	450~455	DCE	75
3	Ru(bpy)₃Cl₂	420~425	DCE	0
4	4CzIPN	420~425	DCE	0
5	Eosin Y	530~535	DCE	58
6	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	THF	12
7	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	Acetone	15
8	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	MeCN	11
9	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	DMSO	5
10	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	-	DCE	0^c
11	$\text{Mes-Acr-M}{{\text{e}}^{\text{+}}}\text{ClO}_{\text{4}}^{-}$	450~455	DCE	0^d