Iron(0)-Mediated Henry-Type Reaction of Bromonitromethane with Aldehydes for the Efficient Synthesis of 2-Nitro-alkan-1-ols

doi:10.6023/cjoc202107048

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 235-241.DOI: 10.6023/cjoc202107048 Previous Articles Next Articles

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铁(0)促进的醛与溴代硝基甲烷的Henry型反应高效合成2-硝基-1-醇

张斯旋^a, 李祥瑞^a, 李文欣^a, 饶卫东^b, 葛丹华^a^,^*(), 沈志良^a, 褚雪强^a^,^*()

a 南京工业大学化学与分子工程学院先进化学制造研究院化学实验教学中心南京 211816
b 南京林业大学化工学院江苏省生物质绿色燃料与化学品重点实验室南京 210037

收稿日期:2021-07-23 修回日期:2021-08-27 发布日期:2021-08-28
通讯作者: 葛丹华, 褚雪强
作者简介:
† 共同第一作者.
基金资助:
南京工业大学科研启动基金(39837118); 南京工业大学科研启动基金(39837146); 国家自然科学基金(22001121); 江苏省自然科学基金(BK20180690)

Iron(0)-Mediated Henry-Type Reaction of Bromonitromethane with Aldehydes for the Efficient Synthesis of 2-Nitro-alkan-1-ols

Sixuan Zhang^a, Xiangrui Li^a, Wenxin Li^a, Weidong Rao^b, Danhua Ge^a(), Zhiliang Shen^a, Xueqiang Chu^a()

a Chemical Experiment Teaching Center, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816
b Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 21003

Received:2021-07-23 Revised:2021-08-27 Published:2021-08-28
Contact: Danhua Ge, Xueqiang Chu
About author:
† These authors contributed equally to this work.
Supported by:
Nanjing Tech University(39837146); National Natural Science Foundation of China(22001121); Natural Science Foundation of Jiangsu Province(BK20180690)

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Abstract

The Henry-type reaction of bromonitromethane with various aldehydes for the efficient synthesis of 2-nitro-alkan- 1-ols by using inexpensive and commercial iron powder as reaction mediator was developed. The reaction proceeded efficiently in the presence of PbCl₂ and tetrabutylammonium hydrogen sulfate (TBAHS) to produce the desired products in moderate to good yield with wide functional group tolerance.

Key words: iron, lead dichloride, Henry-type reaction, bromonitromethane, 2-nitro-alkan-1-ol

Cite this article

Sixuan Zhang, Xiangrui Li, Wenxin Li, Weidong Rao, Danhua Ge, Zhiliang Shen, Xueqiang Chu. Iron(0)-Mediated Henry-Type Reaction of Bromonitromethane with Aldehydes for the Efficient Synthesis of 2-Nitro-alkan-1-ols[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 235-241.

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Entry	Catalyst	Yield^b/%	Entry	Catalyst	Yield^b/%
1 2 3	— InCl₃ BiCl₃	0 25 28	10 11 12	FeBr₂ PbCl₂ PbBr₂	26 58 (53)^c 32
4	MnCl₂	48	13	PbI₂	28
5	CrCl₃	24	14	CuBr	38
6	ZnCl₂	46	15	CuI	26
7	FeCl₃	34	16	NaI	30
8	FeCl₂	22	17	NH₄I	10
9	FeBr₃	26	18	LiI	30

Entry	Catalyst	Yield^b/%	Entry	Catalyst	Yield^b/%
1 2 3	— InCl₃ BiCl₃	0 25 28	10 11 12	FeBr₂ PbCl₂ PbBr₂	26 58 (53)^c 32
4	MnCl₂	48	13	PbI₂	28
5	CrCl₃	24	14	CuBr	38
6	ZnCl₂	46	15	CuI	26
7	FeCl₃	34	16	NaI	30
8	FeCl₂	22	17	NH₄I	10
9	FeBr₃	26	18	LiI	30

Entry	Additive	Yield^b/%
1	TBAB	32
2	TBAI	<5
3	TBAHS	78 (74)^c
4	CTMAB	20
5	KHSO₄	67
6	TsOH	67
7	TBAHS	22^d
8	TBAHS	18^e

Entry	Additive	Yield^b/%
1	TBAB	32
2	TBAI	<5
3	TBAHS	78 (74)^c
4	CTMAB	20
5	KHSO₄	67
6	TsOH	67
7	TBAHS	22^d
8	TBAHS	18^e

铁(0)促进的醛与溴代硝基甲烷的Henry型反应高效合成2-硝基-1-醇

Iron(0)-Mediated Henry-Type Reaction of Bromonitromethane with Aldehydes for the Efficient Synthesis of 2-Nitro-alkan-1-ols

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Entry	Product	Yield^b/%	Entry	Product	Yield^b/%
1	3b	68	10	3k	64
2	3c	63	11	3l	41
3	3d	75	12	3m	36
4	3e	69	13	3n	49
5	3f	65	14	3o	55
6	3g	60	15	3p	45
7	3h	66	16	3q	43
8	3i	85	17	3r	47^c^,^d
9	3j	67

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