Sustainable electrochemical cross-dehydrogenative coupling of 4-quinolones and diorganyl diselenides

doi:10.1016/S1872-2067(20)63750-0

Abstract

Abstract:

An environmentally friendly method for the synthesis of 3-organylselenyl quinolones through the electrochemical cross-dehydrogenative coupling of 4-quinolones and diorganyl diselenides was developed. As a green, atom economic and self-separating process, the present reaction requires neither external oxidants nor electrolytes, forming a recyclable catalytic system.

Key words: Green chemistry, Cross-dehydrogenative coupling, Atom ecomnomy, Reusability, Electrochemistry

Jin-Yang Chen, Hong-Yu Wu, Qing-Wen Gui, Shan-Shu Yan, Jie Deng, Ying-Wu Lin, Zhong Cao, Wei-Min He. Sustainable electrochemical cross-dehydrogenative coupling of 4-quinolones and diorganyl diselenides[J]. Chinese Journal of Catalysis, 2021, 42(9): 1445-1450.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(20)63750-0

https://www.cjcatal.com/EN/Y2021/V42/I9/1445

Figures/Tables 9

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Entry	Variation from the standard reaction conditions	Yield (%)
1	None	99
2	Pt(+)\|Pt(-) instead of C(+)\|Pt(-)	81
3	Ni (+)\|Pt(-) instead of C(+)\|Pt(-)	26
4	RVC(+)\|Pt(-) instead of C(+)\|Pt(-)	81
5	C(+)\|C(-) instead of C(+)\|Pt(-)	85
6	n-Bu₄NI instead of KI	55
7	NH₄I instead of KI	43
8	I₂ instead of KI	61
9	KI (15 mol%) instead of KI (25 mol%)	76
10	ⁿBu₄NBF₄ instead of KI	N. R
11	MeCN as the solvent	52
12	DMF as the solvent	70
13	EtOH as the solvent	trace
14	No electric current	N. R.
15	6 mA instead of 10 mA	53
16	15 mA instead of 10 mA	92


Entry	Variation from the standard reaction conditions	Yield (%)
1	None	99
2	Pt(+)\|Pt(-) instead of C(+)\|Pt(-)	81
3	Ni (+)\|Pt(-) instead of C(+)\|Pt(-)	26
4	RVC(+)\|Pt(-) instead of C(+)\|Pt(-)	81
5	C(+)\|C(-) instead of C(+)\|Pt(-)	85
6	n-Bu₄NI instead of KI	55
7	NH₄I instead of KI	43
8	I₂ instead of KI	61
9	KI (15 mol%) instead of KI (25 mol%)	76
10	ⁿBu₄NBF₄ instead of KI	N. R
11	MeCN as the solvent	52
12	DMF as the solvent	70
13	EtOH as the solvent	trace
14	No electric current	N. R.
15	6 mA instead of 10 mA	53
16	15 mA instead of 10 mA	92