Catalytic Effect of Iron Hydrides on Dehydration of Primary Amides to Nitriles

doi:10.6023/cjoc201903075

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2941-2945.DOI: 10.6023/cjoc201903075 Previous Articles Next Articles

NOTES

铁氢配合物对一级酰胺脱水成腈的催化作用

郑婷婷^a^b, 王洋洋^a^c, 杨在孝^a, 孙宏建^a, 李晓燕^a^*()

a 山东大学化学与化工学院教育部特种功能聚集体材料重点实验室济南 250100
b 首都师范大学化学系北京 100048
c 西北师范大学化学化工学院兰州 730070

收稿日期:2019-03-30 修回日期:2019-06-03 发布日期:2019-07-03
通讯作者: 李晓燕 E-mail:xli63@sdu.edu.cn
基金资助:
国家自然科学基金;国家自然科学基金(No. 21372143)

Catalytic Effect of Iron Hydrides on Dehydration of Primary Amides to Nitriles

Zheng, Tingting^a^b, Wang, Yangyang^a^c, Yang, Zaixiao^a, Sun, Hongjian^a, Li, Xiaoyan^a^*()

a Key Laboratory of Special Functional Aggregated Materials, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100
b Department of Chemistry, Capital Normal University, Beijing 100048
c College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2019-03-30 Revised:2019-06-03 Published:2019-07-03
Contact: Li, Xiaoyan E-mail:xli63@sdu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China;Project supported by the National Natural Science Foundation of China(No. 21372143)

Three cis-selenophenolato iron hydrides [cis-[(ArSe)FeH(PMe₃)₄] (Ar=Ph (1), p-MeOC₆H₄ (2) and o-MeC₆H₄ (3)], were used as catalysts for the dehydration of primary amides to nitriles. The experimental results show that three complexes have good catalytic effect on reductive dehydration of primary amide to nitrile under mild conditions using (EtO)₃SiH as reducing agent. The catalytic system is well tolerated to the substituents on the benzene ring in aromatic amides. Compared with electron-donating group, electron-withdrawing group is more advantageous to the catalytic reaction.

Key words: iron hydride, selenophenol, Se-coordination, reductive amide dehydration, nitrile preparation

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Zheng, Tingting, Wang, Yangyang, Yang, Zaixiao, Sun, Hongjian, Li, Xiaoyan. Catalytic Effect of Iron Hydrides on Dehydration of Primary Amides to Nitriles[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2941-2945.

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Fig. & Tab. 3

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铁氢配合物对一级酰胺脱水成腈的催化作用

Catalytic Effect of Iron Hydrides on Dehydration of Primary Amides to Nitriles

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Entry	Catalyst	Loading/mol%	Silane	Solvent	T/℃	t/h	Conv.^b/%
1	Fe(PMe₃)₄	2	(EtO)₃SiH	THF	60	24	0
2	2	2	(EtO)₃SiH	THF	60	24	77
3	3	2	(EtO)₃SiH	THF	60	24	54
4	1	2	(EtO)₃SiH	THF	60	24	99
5	1	1	(EtO)₃SiH	THF	60	24	82
6	1	2	Et₃SiH	THF	60	24	23
7	1	2	PhSiH₃	THF	60	24	30
8	1	2	Ph₂SiH₂	THF	60	24	61
9	1	2	Ph₃SiH	THF	60	24	0
10	1	2	TMDS	THF	60	24	28
11	1	2	PMHS	THF	60	24	0
12	1	2	(EtO)₃SiH	Toluene	60	24	87
13	1	2	(EtO)₃SiH	Pentane	60	24	25
14	1	2	(EtO)₃SiH	DMF	60	24	46
15	1	2	(EtO)₃SiH	DMSO	60	24	79
16	1	2	(EtO)₃SiH	Dioxane	60	24	85
17	1	2	(EtO)₃SiH	CH₃CN	60	24	63
18	1	2	(EtO)₃SiH	THF	50	24	90
19	1	2	(EtO)₃SiH	THF	55	24	97
20	1	2	(EtO)₃SiH	THF	60	13	58
21	1	2	(EtO)₃SiH	THF	60	16	78
22	1	2	(EtO)₃SiH	THF	60	20	94