Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C—C Bond Cleavage

doi:10.6023/cjoc202403007

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2233-2240.DOI: 10.6023/cjoc202403007 Previous Articles Next Articles

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银催化环丙烯酮与醇的C—C键断裂加成反应

张书林, 张周, 孙萌^*()

西北大学化学与材料科学学院合成与天然功能分子教育部重点实验室西安 710127

收稿日期:2024-03-05 修回日期:2024-03-20 发布日期:2024-04-24
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(21702160); 大连理工大学精细化工国家重点实验室(KF2311)

Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C—C Bond Cleavage

Shulin Zhang, Zhou Zhang, Meng Sun()

Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710127

Received:2024-03-05 Revised:2024-03-20 Published:2024-04-24
Contact: * E-mail: sunmeng@nwu.edu.cn
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21702160); State Key Laboratory of Fine Chemicals, Dalian University of Technology(KF2311)

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Abstract

An efficient method for the synthesis of α-phenylcinnamates via silver catalyzed C—C bond activation reaction of cyclopropenone and alcohol was developed. This protocol features a simple reaction system, specific regioselectivity, good functional group compatibility and good yields. It is of great significance for the later modification of natural products.

Key words: silver catalysis, C—C bond activation, cyclopropenone, nucleophilic addition

Cite this article

Shulin Zhang, Zhou Zhang, Meng Sun. Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C—C Bond Cleavage[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2233-2240.

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Fig. & Tab. 8

Figure 1. Selected examples of α-phenylcinnamate-containing natural products

Scheme 1. Ways of synthesis of α-phenylcinnamates with cyclopropenones via C—C bond cleavage

Entry	Catalyst	Solvent	Yield/%
1	AgBF₄	THF	63
2	AgBF₄	DCE	65
3	AgBF₄	DME	72
4	AgBF₄	MeCN	56
5	AgBF₄	Toluene	92
6	AgSbF₆	Toluene	48
7	AgNTf₂	Toluene	43
8	AgOTf	Toluene	54
9^c	AgBF₄	Toluene	74
10^d	AgBF₄	Toluene	81
11		Toluene	n.r.

Table 1. Screening of reaction conditionsa,b

Table 2. Scope of alcoholsa,b

Table 3. Scope of cyclopropenonesa,b

Scheme 2. Scale-up of the reaction and derivatization of the products

Scheme 3. Mechanistic studies

Scheme 4. Possible reaction mechanism

References 12

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银催化环丙烯酮与醇的C—C键断裂加成反应

Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C—C Bond Cleavage

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