Potassium Hexamethyldisilazide-Catalyzed Synthesis of 1,3,5-Triaroyl Cyclohexanes

doi:10.6023/cjoc202408014

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (4): 1402-1410.DOI: 10.6023/cjoc202408014 Previous Articles Next Articles

双(三甲基硅基)氨基钾催化合成1,3,5-三芳甲酰基环己烷

高娜娜^a, 姚志刚^b^,^*(), 徐凡^a^,^*()

a 苏州大学材料与化学化工学部苏州 215123
b 苏州大学分析测试中心苏州 215123

收稿日期:2024-08-12 修回日期:2024-09-22 发布日期:2024-11-08
基金资助:
国家重点研发计划(2020YFC1808601)

Potassium Hexamethyldisilazide-Catalyzed Synthesis of 1,3,5-Triaroyl Cyclohexanes

Nana Gao^a, Zhigang Yao^b(), Fan Xu^a()

a College of Chemistry, Chemical Engineering and Material Science, Soochow University, Suzhou 215123
b Analysis and Testing Center, Soochow University, Suzhou 215123

Received:2024-08-12 Revised:2024-09-22 Published:2024-11-08
Contact: * E-mail: zhgyao@suda.edu.cn; xufan@suda.edu.cn
Supported by:
National Key Research and Development Program of China(2020YFC1808601)

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Abstract

1,3,5-Triaroyl cyclohexane is highly valuable due to its uniqueness of structure. The development of a catalytic and efficient method for the synthesis of 1,3,5-triaroyl cyclohexane is of great value. The cyclotrimerization of chalcones catalyzed by potassium hexamethyldisilazide is described, which effectively produces a series of 1,3,5-triaroyl cyclohexanes in moderate to high yields. A mechanism involving sequential Michael addition catalyzed by silylamide anion is proposed. This method provides a simple, efficient, and atom-economical route for the synthesis of 1,3,5-triaroyl cyclohexanes.

Key words: potassium hexamethyldisilazide, triaroyl cyclohexane, cyclotrimerization, catalysis

Cite this article

Nana Gao, Zhigang Yao, Fan Xu. Potassium Hexamethyldisilazide-Catalyzed Synthesis of 1,3,5-Triaroyl Cyclohexanes[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1402-1410.

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Fig. & Tab. 6

References 18

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Entry	Catalyst	Yield^b/% of 2a
1	LiN(SiMe₃)₂	50^c
2	Et₃N	0
3	DBU	0
4	Cs₂CO₃	0
5	KOH	0
6	ⁿBuLi	16^c
7	NaN(SiMe₃)₂	52^c
8	KN(SiMe₃)₂	68^c

Entry	Catalyst	Yield^b/% of 2a
1	LiN(SiMe₃)₂	50^c
2	Et₃N	0
3	DBU	0
4	Cs₂CO₃	0
5	KOH	0
6	ⁿBuLi	16^c
7	NaN(SiMe₃)₂	52^c
8	KN(SiMe₃)₂	68^c

双(三甲基硅基)氨基钾催化合成1,3,5-三芳甲酰基环己烷

Potassium Hexamethyldisilazide-Catalyzed Synthesis of 1,3,5-Triaroyl Cyclohexanes

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References 18

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Entry	Solvent	Temp./℃	t/h	Catalyst loading/mol%	Yield^b/%
1	DMF	60	12	30	Trace
2	CH₃CN	60	12	30	Trace
3	1,4-Dioxane	60	12	30	11
4	THF	60	12	30	14
5	DCE	60	12	30	Trace
6	PhCl	60	12	30	30
7	Toluene	60	12	30	68
8	Toluene	r.t.	12	30	61
9	Toluene	40	12	30	75 (74)^c
10	Toluene	75	12	30	57
11	Toluene	90	12	30	45
12^c	Toluene	40	8	30	75
13^c	Toluene	40	4	30	75
14^c	Toluene	40	2	30	68
15^c	Toluene	40	4	15	82
16^c	Toluene	40	4	10	86
17^c	Toluene	40	4	5	68
18^c	Toluene	40	4	0	0

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