Reaction of Tandem Addition of Aliphatic Amines to Alkenylnitriles Catalyzed by Tris(o-dimethylaminobenzyl)yttrium

doi:10.6023/cjoc202203002

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2070-2078.DOI: 10.6023/cjoc202203002 Previous Articles Next Articles

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三(邻二甲胺基苄基)钇催化脂肪胺对烯腈的插入串联反应

侯金松^a^,^b, 杨高升^a^,^*()

^a安徽师范大学化学与材料科学学院有机化学研究所安徽省分子材料重点实验室功能分子固体教育部重点实验室安徽芜湖 241002
^b滁州学院材料与化学工程学院安徽滁州 239000

收稿日期:2022-03-01 修回日期:2022-04-05 发布日期:2022-08-09
通讯作者: 杨高升
基金资助:
国家自然科学基金(21672005); 国家自然科学基金(20972001)

Reaction of Tandem Addition of Aliphatic Amines to Alkenylnitriles Catalyzed by Tris(o-dimethylaminobenzyl)yttrium

Jinsong Hou^a^,^b, Gaosheng Yang^a()

^aMOE Key Laboratory of Functional Molecular Solids, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241002
^bCollege of Material and Chemical Engineering, Chuzhou University, Chuzhou, Anhui 239000

Received:2022-03-01 Revised:2022-04-05 Published:2022-08-09
Contact: Gaosheng Yang
Supported by:
National Natural Science Foundation of China(21672005); National Natural Science Foundation of China(20972001)

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Abstract

Amidines are nitrogen-containing compounds with very important physiological activities. There are few reports on the synthesis of cyclic amidines catalyzed by rare earth complexes. In this paper, a series of cyclic amidines were synthesized by the tandem reaction of N—H to CN and “C=C” with simple trialkyl rare earth metal complex Y(CH₂C₆H₄NMe₂-o)₃ as precatalyst with 22%~96% yields. The method has the characteristics of simple catalyst, mild reaction conditions and 100% atomic utilization. It provides a new way for the construction of cyclic amidines.

Key words: rare earth metal complexes, tandem reaction, aliphatic amine, amidine, synthesis

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Jinsong Hou, Gaosheng Yang. Reaction of Tandem Addition of Aliphatic Amines to Alkenylnitriles Catalyzed by Tris(o-dimethylaminobenzyl)yttrium[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2070-2078.

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Fig. & Tab. 7

References 14

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三(邻二甲胺基苄基)钇催化脂肪胺对烯腈的插入串联反应

Reaction of Tandem Addition of Aliphatic Amines to Alkenylnitriles Catalyzed by Tris(o-dimethylaminobenzyl)yttrium

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Entry	Catalyst	t/h	Conv.^b/%
1	Y[N(SiMe₃)₂]₃	93	98
2	Y[N(SiMe₃)₂]₃(μ-Cl)Li(THF)₃	93	99
3	Y(CH₂SiMe₃)₃(THF)₂	19	99
4	Y(o-C₆H₄CH₂NMe₂)₃	20	99
5	Y(CH₂C₆H₄NMe₂-o)₃	20	99
6	Sc(CH₂SiMe₃)₃(THF)₂	84	86
7	Lu(CH₂SiMe₃)₃(THF)₂	26	95
8	Sc(CH₂C₆H₄NMe₂-o)₃	82	90
9	Lu(CH₂C₆H₄NMe₂-o)₃	26	98
10	Sm(CH₂C₆H₄NMe₂-o)₃	38	99
11	La(CH₂C₆H₄NMe₂-o)₃	57	85
12^c	Y(CH₂C₆H₄NMe₂-o)₃	30	98
13^d	Y(CH₂C₆H₄NMe₂-o)₃	40	99
14^e	Y(CH₂C₆H₄NMe₂-o)₃	10	94
15^f	Y(CH₂C₆H₄NMe₂-o)₃	10	99 (95)