Base-Promoted Ring Expansion Reactions for the Construction of Cycloheptanones through C—C Bond Cleavage

doi:10.6023/cjoc202101031

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2715-2722.DOI: 10.6023/cjoc202101031 Previous Articles Next Articles

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基于C—C键断裂碱促进扩环构建环庚酮化合物

王微, 崔雪, 马健婷, 李友宾^*(), 王雪松^*()

海南医学院药学院热带转化医学教育部重点实验室海南省热带药用植物研究开发重点实验室海口市黎族医药重点实验室海口 571199

收稿日期:2021-01-18 修回日期:2021-04-08 发布日期:2021-04-25
通讯作者: 李友宾, 王雪松
作者简介:
† 共同第一作者(These authors contributed equally to this work).
基金资助:
海南省自然科学青年基金(820QN264); 2019年海南省基础与应用基础研究计划(自然科学领域)高层次人才基金(2019RC214); 海南医学院引进人才启动基金(XRC180009)

Base-Promoted Ring Expansion Reactions for the Construction of Cycloheptanones through C—C Bond Cleavage

Wei Wang, Xue Cui, Jianting Ma, Youbin Li(), Xuesong Wang()

Key Laboratory of Tropical Translational Medicine of Ministry of Education, Hainan Provincial Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Hainan Medical University, Haikou 571199

Received:2021-01-18 Revised:2021-04-08 Published:2021-04-25
Contact: Youbin Li, Xuesong Wang
Supported by:
Hainan Provincial Natural Science Youth Foundation of China(820QN264); High-level Talents Fund of Basic and Applied Basic Research Program (Natural Science) of Hainan Province in 2019(2019RC214); Talent Introduction Start-up Fund of Hainan Medical University(XRC180009)

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Abstract

An efficient ring expansion strategy has been developed for the construction of cycloheptanones through C—C bond cleavage. The reactions take place with easily accessible starting materials, good functional group tolerance, and mild reaction conditions in the presence of Cs₂CO₃ without any metal or oxidant reagent. The transition-metal free insertions of alkynes into carbon-carbon σ-bonds of acenaphthenone initialized through intramolecular nucleophilic addition/ring-opening to furnish multifarious cycloheptanones, which has the potential to be widely utilized in organic synthetic chemistry.

Key words: C—C bond cleavage, ring expansion, base-promoted, cycloheptanone compounds

Cite this article

Wei Wang, Xue Cui, Jianting Ma, Youbin Li, Xuesong Wang. Base-Promoted Ring Expansion Reactions for the Construction of Cycloheptanones through C—C Bond Cleavage[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2715-2722.

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基于C—C键断裂碱促进扩环构建环庚酮化合物

Base-Promoted Ring Expansion Reactions for the Construction of Cycloheptanones through C—C Bond Cleavage

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Fig. & Tab. 5

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Entry	Base	Solvent	Time/h	Yield^b/%
1	K₂CO₃	DMSO	12	28
2	Cs₂CO₃	DMSO	2	78
3	NaOH	DMSO	2	51
4	KOH	DMSO	2	58
5	NaH	DMSO	2	45
6	NaO^tBu	DMSO	2	68
7	KO^tBu	DMSO	2	62
8	Cs₂CO₃	DMF	2	82
9	Cs₂CO₃	DMAC	2	82
10	Cs₂CO₃	CH₃CN	12	Trace
11	Cs₂CO₃	THF	12	Trace
12	Cs₂CO₃	H₂O	12	Trace
13	Cs₂CO₃	Toluene	12	Trace
14	Cs₂CO₃	EtOH	12	Trace
15	Cs₂CO₃	1,4-Dioxane	12	Trace
16	Cs₂CO₃	CH₂Cl₂	12	Trace
17^c	Cs₂CO₃	DMF	2	72
18^d	Cs₂CO₃	DMF	2	78
19^e	Cs₂CO₃	DMF	2	83

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