Manganese-Catalyzed Allylation of Quinazolinones with 4-Vinyl-1,3-dioxolan-2-one via C—H Activation

doi:10.6023/cjoc202110002

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 847-853.DOI: 10.6023/cjoc202110002 Previous Articles Next Articles

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锰催化的碳酸乙烯亚乙酯对喹唑啉酮的C—H烯丙基化

李玉东^a^,^b, 李莹^a, 董亚楠^a, 夏春谷^a^,^*(), 李跃辉^a^,^*()

a 中国科学院兰州化学物理研究所苏州研究院羰基合成与选择氧化国家重点实验室兰州 730000
b 中国科学院大学北京 100049

收稿日期:2021-10-02 修回日期:2021-10-30 发布日期:2021-11-09
通讯作者: 夏春谷, 李跃辉
基金资助:
国家自然科学基金(22022204); 国家自然科学基金(21633013); 国家自然科学基金(22072167)

Manganese-Catalyzed Allylation of Quinazolinones with 4-Vinyl-1,3-dioxolan-2-one via C—H Activation

Yudong Li^a^,^b, Ying Li^a, Ya'nan Dong^a, Chungu Xia^a(), Yuehui Li^a()

a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000
b University of Chinese Academy of Sciences, Beijing 100049

Received:2021-10-02 Revised:2021-10-30 Published:2021-11-09
Contact: Chungu Xia, Yuehui Li
Supported by:
National Natural Science Foundation of China(22022204); National Natural Science Foundation of China(21633013); National Natural Science Foundation of China(22072167)

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Abstract

The ortho-allylation of quinazolinones with 4-vinyl-1,3-dioxolan-2-one via manganese catalysis has been described. A series of allylation products with potential applications have been obtained. This protocol is also highlighted by good compatibility of functional groups and excellent E/Z selectivity. This work broadens the scope of Mn-catalyzed C—C coupling reactions.

Key words: manganese-catalyzed, allylation, quinazolinones, C—H activation

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Yudong Li, Ying Li, Ya'nan Dong, Chungu Xia, Yuehui Li. Manganese-Catalyzed Allylation of Quinazolinones with 4-Vinyl-1,3-dioxolan-2-one via C—H Activation[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 847-853.

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Entry	[Mn]	Solvent	Base	Yield^b/%
1	—	DMF	—	0
2	MnBr(CO)₅	DMF	—	45 (E/Z=9.4)
3	MnBr₂	DMF	—	0
4	MnCl₂	DMF	—	0
5	Mn(OAc)₂	DMF	—	0
6	MnBr(CO)₅	DMF	KOAc	54 (E/Z=8.3)
7	MnBr(CO)₅	DMF	NaOAc	68 (E/Z=8.2)
8	MnBr(CO)₅	DMF	LiOAc	46 (E/Z=7.4)
9	MnBr(CO)₅	DMF	K₃PO₄	31 (E/Z=8.1)
10	MnBr(CO)₅	DMF	CsF	33 (E/Z=7.9)
11	MnBr(CO)₅	DMF	Cy₂NH	28 (E/Z=8.7)
12	MnBr(CO)₅	1,4-Dioxane	NaOAc	17 (E/Z=4.3)
13	MnBr(CO)₅	DMA	NaOAc	50 (E/Z=8.8)
14	MnBr(CO)₅	THF	NaOAc	12 (E/Z=3.6)
15	MnBr(CO)₅	DMSO	NaOAc	25 (E/Z=7.5)
16	MnBr(CO)₅	DCE	NaOAc	Trace
17	MnBr(CO)₅	NMP	NaOAc	82 (E/Z=9.4)
18^c	MnBr(CO)₅	NMP	NaOAc	90 (E/Z=9.5)
19^d	MnBr(CO)₅	NMP	NaOAc	89 (E/Z=9.4)
20^e	MnBr(CO)₅	NMP	NaOAc	62 (E/Z=9.5)
21^f	MnBr(CO)₅	NMP	NaOAc	73 (E/Z=9.6)

Entry	[Mn]	Solvent	Base	Yield^b/%
1	—	DMF	—	0
2	MnBr(CO)₅	DMF	—	45 (E/Z=9.4)
3	MnBr₂	DMF	—	0
4	MnCl₂	DMF	—	0
5	Mn(OAc)₂	DMF	—	0
6	MnBr(CO)₅	DMF	KOAc	54 (E/Z=8.3)
7	MnBr(CO)₅	DMF	NaOAc	68 (E/Z=8.2)
8	MnBr(CO)₅	DMF	LiOAc	46 (E/Z=7.4)
9	MnBr(CO)₅	DMF	K₃PO₄	31 (E/Z=8.1)
10	MnBr(CO)₅	DMF	CsF	33 (E/Z=7.9)
11	MnBr(CO)₅	DMF	Cy₂NH	28 (E/Z=8.7)
12	MnBr(CO)₅	1,4-Dioxane	NaOAc	17 (E/Z=4.3)
13	MnBr(CO)₅	DMA	NaOAc	50 (E/Z=8.8)
14	MnBr(CO)₅	THF	NaOAc	12 (E/Z=3.6)
15	MnBr(CO)₅	DMSO	NaOAc	25 (E/Z=7.5)
16	MnBr(CO)₅	DCE	NaOAc	Trace
17	MnBr(CO)₅	NMP	NaOAc	82 (E/Z=9.4)
18^c	MnBr(CO)₅	NMP	NaOAc	90 (E/Z=9.5)
19^d	MnBr(CO)₅	NMP	NaOAc	89 (E/Z=9.4)
20^e	MnBr(CO)₅	NMP	NaOAc	62 (E/Z=9.5)
21^f	MnBr(CO)₅	NMP	NaOAc	73 (E/Z=9.6)

锰催化的碳酸乙烯亚乙酯对喹唑啉酮的C—H烯丙基化

Manganese-Catalyzed Allylation of Quinazolinones with 4-Vinyl-1,3-dioxolan-2-one via C—H Activation

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