The samarium triiodide promoted the conjugate  addition of aromatic amines to α,β-unsaturated  nitriles(esters)

Abstract

Promoted by samarium triiodide, the conjugate addition reaction of aromatic amines with α,β-unsaturated nitriles or esters takesplace easily under mild and neutral condition and yield the corresponding β -amino nitriles and β-amino esters respectively in satisfactory yields. The mechanism of the reaction is also discussed.

Key words: ACCELERATORS, AMINONITRILE, IODINE COMPOUNDS, SAMARIUM COMPOUNDS, CONJUGATE, ADDITION REACTION, REACTION MECHANISM, ORGANOMETALLIC REACTION

CLC Number:

O627

Cite this article

Zhong Weihui;Zhang Yongmin. The samarium triiodide promoted the conjugate addition of aromatic amines to α,β-unsaturated nitriles(esters)[J]. Chin. J. Org. Chem., 2000, 20(5): 747-749.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Tongyang Cao, Wei Li, Lijing Wang. Recent Progress in N-Iodosuccinimide (NIS)-Mediated Iodination Reactions [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 508-524.
[2]	Min Xi, Chao Duan, Jie Chi, Tian Fu, Xiaolong Su, Hongshe Wang. An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3312-3318.
[3]	Zujia Chen, Shiwei Yu, Yongjun Zhou, Huanqing Li, Qiwen Qiu, Miaoxin Li, Zhaoyang Wang. Application of BF₃•OEt₂ in Organic Synthesis as a Catalyst or Synthon [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3107-3118.
[4]	Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.
[5]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[6]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[7]	Lin Zhou, Hong Yang, Chuan Yang, Zhigang Zhao, Qinghan Li. Advances on the α- and β-Reactions of Deconjugated Butenolides [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2407-2424.
[8]	Guangli Xu, Jing Xu, Haidong Xu, Xiang Cui, Xingzhong Shu. Research Progress of Transition Metal Catalyzed Synthesis of 1,3- Conjugated Diene Compounds from Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1899-1933.
[9]	Min Lü, Aimei Yang, Yu Zhang, Jianting Sun, Bangguo Wei. Fe(OTf)₃-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1777-1785.
[10]	Deliang Kong, Wen Dai, Yiling Zhao, Yilin Chen, Hongping Zhu. Study on Oxidative Cycloaddition Reactions of Amidinatoboryl-aminosilylenes toward Ketone and Diketone Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1843-1851.
[11]	Cunjing Miao, Jiaqi Yao. Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1341-1364.
[12]	Wenlong Chen, Huimin Li, Pengfei Yang, Dongcheng Zheng, Gaosheng Yang. Reaction of 2-Aroylmethylenemalonates with Corey Ylide [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1472-1482.
[13]	Luomo Li, Xiaohui Yang. Recent Advances in Ionic Transfer Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1036-1044.
[14]	Kongchuan Wu, Kaihong Lu, Jianbin Lin, Huijun Zhang. Research Progress in Ortho-C—H Bond Functionalization of Rylene Diimides [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1000-1011.
[15]	Yueling Liu, Xinxin Zhong, Ganbing Zhang. Density Functional Theory Study for Exploring the Mechanisms of the [3＋2] Cycloaddition Reactions between 1-R-3-Phenylpropylidenecyclopropane (R=Me/H) and Furfural Catalyzed by Pd(0) [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 660-667.

三碘化钐促进的芳胺与α,β-不饱和腈(酯)的共轭加成