Research for the t-BuOK-Catalyzed Synthesis of Aromatic Aldehydes and Ketone from Arylmethyl Azides

doi:10.6023/cjoc201605045

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 97-102.DOI: 10.6023/cjoc201605045 Previous Articles Next Articles

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叔丁醇钾催化芳甲基叠氮化合物合成芳醛和芳酮的反应研究

黄青兰, 谭志强, 于长江, 朱晓敏, 吴禄勇

海南师范大学热带药用植物化学教育部重点实验室海口 571158

收稿日期:2016-05-30 修回日期:2016-08-14 发布日期:2016-09-22
通讯作者: 吴禄勇 E-mail:wuluyong@hainnu.edu.cn
基金资助:
国家自然科学基金（No. 21362008）、海南省大学生创新创业训练计划（No. 20140062）资助项目.

Research for the t-BuOK-Catalyzed Synthesis of Aromatic Aldehydes and Ketone from Arylmethyl Azides

Huang Qinglan, Tan Zhiqiang, Yu Changjiang, Zhu Xiaoming, Wu Luyong

Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158

Received:2016-05-30 Revised:2016-08-14 Published:2016-09-22
Supported by:
Project supported by the National Natural Sciences Foundation of China(No. 21362008) and the Undergraduate Innovation and Entrepreneurship Training Program of Henan Province(No. 20140062).

1. Research for the t-BuOK-Catalyzed Synthesis of Aromatic Aldehydes and Ketone from Arylmethyl Azides.PDF(1664KB)

Abstract

A novel synthesis of aromatic aldehyde from arylmethyl azides has been explored via base-mediated N₂-extrusion and hydrolyzation.The effects of bases,hydrolysis conditions and the amount of base used on the reaction were also investigated.Benzaldehyde was isolated in the best yield of 83%,when the reaction was carried in N,N-dimethylformamide(DMF) and catalyzed by t-BuOK.Meanwhile,a variety of azides were investigated,and it was found that substituted benzyl azides could give the corresponding aromatic aldehydes in the yield of 38%~87%.The reaction of heteoaryl methyl azides was less efficient.According to the controlling experiments,the mechanism has been quitted.

Key words: arylmethyl azides, N₂-extrusion, aryl aldehydes, t-BuOK

Cite this article

Huang Qinglan, Tan Zhiqiang, Yu Changjiang, Zhu Xiaoming, Wu Luyong. Research for the t-BuOK-Catalyzed Synthesis of Aromatic Aldehydes and Ketone from Arylmethyl Azides[J]. Chin. J. Org. Chem., 2017, 37(1): 97-102.

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叔丁醇钾催化芳甲基叠氮化合物合成芳醛和芳酮的反应研究

Research for the t-BuOK-Catalyzed Synthesis of Aromatic Aldehydes and Ketone from Arylmethyl Azides

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