1,4-Diazabicyclo[2.2.2]octane-Promoted Addition Reaction of Tricarbonyl Monohydrates with Active Alkynes via Consecutive C—C/C—O Cleavage

doi:10.6023/cjoc202104016

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4384-4390.DOI: 10.6023/cjoc202104016 Previous Articles Next Articles

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1,4-二氮杂二环[2.2.2]辛烷促进三酮单水合物和活泼炔通过连续碳-碳/碳-氧键断裂的加成反应

张金凤, 叶如意, 李子阳, 孟令国^*()

淮北师范大学化学与材料科学学院安徽淮北 235000

收稿日期:2021-04-08 修回日期:2021-06-01 发布日期:2021-08-17
通讯作者: 孟令国
基金资助:
安徽高校自然科学研究基金(KJ2020A0045); 安徽高校自然科学研究基金(KJ2020B01)

1,4-Diazabicyclo[2.2.2]octane-Promoted Addition Reaction of Tricarbonyl Monohydrates with Active Alkynes via Consecutive C—C/C—O Cleavage

Jinfeng Zhang, Ruyi Ye, Ziyang Li, Lingguo Meng()

School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000

Received:2021-04-08 Revised:2021-06-01 Published:2021-08-17
Contact: Lingguo Meng
Supported by:
Natural Science Foundation of Educational Committee of Anhui Province(KJ2020A0045); Natural Science Foundation of Educational Committee of Anhui Province(KJ2020B01)

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Abstract

A novel addition reaction of vicinal tricarbonyl monohydrates with active alkynes proceeded via rapid consecutive C—C/C—O cleavage processes under metal-free and mild reaction conditions, and the transformation was completed within only 1 min. Diverse tricarbonyl monohydrates could react with active alkynes to produce carboxylate esters via these transformations in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).

Key words: C—C cleavage, C—O cleavage, addition, promoter

Cite this article

Jinfeng Zhang, Ruyi Ye, Ziyang Li, Lingguo Meng. 1,4-Diazabicyclo[2.2.2]octane-Promoted Addition Reaction of Tricarbonyl Monohydrates with Active Alkynes via Consecutive C—C/C—O Cleavage[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4384-4390.

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Fig. & Tab. 6

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Entry	Solvent	Base	Yield^b
1	CH₂Cl₂	DABCO	25^c
2	CH₂Cl₂	DABCO	36^d
3	CH₂Cl₂	DABCO	45
4	CH₂Cl₂	DABCO	18^e
5	CH₂Cl₂	DABCO	<10^f
6	CH₂Cl₂	DABCO	Complex^g
7	CH₂Cl₂	Et₃N	13
8	CH₂Cl₂	Pyridine	Trace
9	CH₂Cl₂	DBU	Trace
10	CH₂Cl₂	DMAP	ND^h
11	CH₂Cl₂	HMTA	NRⁱ
12	CH₂Cl₂	PPh₃	ND^h
13	CH₂Cl₂	K₂CO₃	NRⁱ
14	CH₂Cl₂	KOBu^t	NRⁱ
15	CHCl₃	DABCO	17
16	THF	DABCO	12
17	CCl₄	DABCO	Trace
18	CH₃CN	DABCO	Trace
19	CS₂	DABCO	Trace
20	Toluene	DABCO	Trace
21	EtOAc	DABCO	Trace
22	DMF	DABCO	ND^h

Entry	Solvent	Base	Yield^b
1	CH₂Cl₂	DABCO	25^c
2	CH₂Cl₂	DABCO	36^d
3	CH₂Cl₂	DABCO	45
4	CH₂Cl₂	DABCO	18^e
5	CH₂Cl₂	DABCO	<10^f
6	CH₂Cl₂	DABCO	Complex^g
7	CH₂Cl₂	Et₃N	13
8	CH₂Cl₂	Pyridine	Trace
9	CH₂Cl₂	DBU	Trace
10	CH₂Cl₂	DMAP	ND^h
11	CH₂Cl₂	HMTA	NRⁱ
12	CH₂Cl₂	PPh₃	ND^h
13	CH₂Cl₂	K₂CO₃	NRⁱ
14	CH₂Cl₂	KOBu^t	NRⁱ
15	CHCl₃	DABCO	17
16	THF	DABCO	12
17	CCl₄	DABCO	Trace
18	CH₃CN	DABCO	Trace
19	CS₂	DABCO	Trace
20	Toluene	DABCO	Trace
21	EtOAc	DABCO	Trace
22	DMF	DABCO	ND^h

1,4-二氮杂二环[2.2.2]辛烷促进三酮单水合物和活泼炔通过连续碳-碳/碳-氧键断裂的加成反应

1,4-Diazabicyclo[2.2.2]octane-Promoted Addition Reaction of Tricarbonyl Monohydrates with Active Alkynes via Consecutive C—C/C—O Cleavage

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