Reaction of Synthesizing α-Hydroxyamides from α-Ketoamides by Using Diiodine/Hydrosilane System

doi:10.6023/cjoc202502026

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (12): 4417-4424.DOI: 10.6023/cjoc202502026 Previous Articles Next Articles

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单质碘/氢硅烷体系作用下由α-酮酰胺合成α-羟基酰胺的反应

冯思燕, 王卓, 蒋金^*()

四川轻化工大学化学与环境工程学院四川自贡 643000

收稿日期:2025-05-19 修回日期:2025-06-10 发布日期:2025-07-11
通讯作者: 蒋金
基金资助:
四川省自然科学基金(2022NSFSC1241)

Reaction of Synthesizing α-Hydroxyamides from α-Ketoamides by Using Diiodine/Hydrosilane System

Siyan Feng, Zhuo Wang, Jin Jiang^*()

School of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong, Sichuan 643000

Received:2025-05-19 Revised:2025-06-10 Published:2025-07-11
Contact: Jin Jiang
Supported by:
Natural Science Foundation of Sichuan Province(2022NSFSC1241)

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Abstract

Both molecular iodine and hydrosilane are compounds that are easy to store and access, and the reactions involving them have the characteristic of simple operation. In this work, diiodine/hydrosilane system is used for the synthesis of α-hydroxyamides. α-Ketoamides are used as the raw materials with chlorodimethylsilane serving as the hydrosilane, and the solvent is ethyl acetate. The synthesis can be achieved within 40 min at room temperature. This synthesis method is easy to operate, and has a short reaction time, a wide range of substrate scope and good functional group tolerance. A total of 22 α-hydroxyamide products were obtained, and a gram-scale experiment was conducted using 2-oxo-2-phenyl-N-(p-tolyl)aceta- mide as the starting material.

Key words: molecular iodine, hydrosilane, chlorodimethylsilane, α-hydroxyamides

Cite this article

Siyan Feng, Zhuo Wang, Jin Jiang. Reaction of Synthesizing α-Hydroxyamides from α-Ketoamides by Using Diiodine/Hydrosilane System[J]. Chinese Journal of Organic Chemistry, 2025, 45(12): 4417-4424.

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Entry	Hydrosilane	Solvent	Yield^b/%
1	Et₃SiH	DCM	71
2	Et₃SiH	EtOAc	72
3	Et₃SiH	MeCN	Trace
4	Et₃SiH	CHCl₃	22
5	Et₃SiH	THF	71
6	Et₃SiH	Toluene	10
7	Et₃SiH	1,4-Dioxane	16
8	Et₃SiH	CH₃NO₂	58
9	Et₃SiH	C₆H₅NO₂	20
10	Et₃SiH	DMF	0
11	Et₃SiH	EtOH	0
12	Et₃SiH	H₂O	0
13	PMHS	EtOAc	78
14	TMDS	EtOAc	81
15	Ph₃SiH	EtOAc	17
16	Ph₂SiH₂	EtOAc	69
17	(EtO)₃SiH	EtOAc	Trace
18	DMCS	EtOAc	98
19^c	DMCS	EtOAc	85

Entry	Hydrosilane	Solvent	Yield^b/%
1	Et₃SiH	DCM	71
2	Et₃SiH	EtOAc	72
3	Et₃SiH	MeCN	Trace
4	Et₃SiH	CHCl₃	22
5	Et₃SiH	THF	71
6	Et₃SiH	Toluene	10
7	Et₃SiH	1,4-Dioxane	16
8	Et₃SiH	CH₃NO₂	58
9	Et₃SiH	C₆H₅NO₂	20
10	Et₃SiH	DMF	0
11	Et₃SiH	EtOH	0
12	Et₃SiH	H₂O	0
13	PMHS	EtOAc	78
14	TMDS	EtOAc	81
15	Ph₃SiH	EtOAc	17
16	Ph₂SiH₂	EtOAc	69
17	(EtO)₃SiH	EtOAc	Trace
18	DMCS	EtOAc	98
19^c	DMCS	EtOAc	85

单质碘/氢硅烷体系作用下由α-酮酰胺合成α-羟基酰胺的反应

Reaction of Synthesizing α-Hydroxyamides from α-Ketoamides by Using Diiodine/Hydrosilane System

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References 26

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Entry	Yield^b/%	Entry	Yield^b/%
1	98	12	53
2	98	13	65
3	60	14	74
4	73	15	75
5	97	16	71
6	58	17	71
7	82	18	67
8	67	19	85
9	89	20	66
10	72	21	52
11	85	22	53

Entry	Yield^b/%	Entry	Yield^b/%
1	98	12	53
2	98	13	65
3	60	14	74
4	73	15	75
5	97	16	71
6	58	17	71
7	82	18	67
8	67	19	85
9	89	20	66
10	72	21	52
11	85	22	53

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Entry	Yield^b/%	Entry	Yield^b/%
1	98	12	53
2	98	13	65
3	60	14	74
4	73	15	75
5	97	16	71
6	58	17	71
7	82	18	67
8	67	19	85
9	89	20	66
10	72	21	52
11	85	22	53

Entry	Yield^b/%	Entry	Yield^b/%
1	98	12	53
2	98	13	65
3	60	14	74
4	73	15	75
5	97	16	71
6	58	17	71
7	82	18	67
8	67	19	85
9	89	20	66
10	72	21	52
11	85	22	53

Entry	Yield^b/%	Entry	Yield^b/%
1	98	12	53
2	98	13	65
3	60	14	74
4	73	15	75
5	97	16	71
6	58	17	71
7	82	18	67
8	67	19	85
9	89	20	66
10	72	21	52
11	85	22	53

Entry	Yield^b/%	Entry	Yield^b/%
1	98	12	53
2	98	13	65
3	60	14	74
4	73	15	75
5	97	16	71
6	58	17	71
7	82	18	67
8	67	19	85
9	89	20	66
10	72	21	52
11	85	22	53