Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives

doi:10.6023/cjoc202207031

Abstract

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

Cite this article

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

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