Citation: 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]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 97-102. doi: 10.6023/cjoc201605045 shu

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

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

Corresponding author: Wu Luyong, wuluyong@hainnu.edu.cn
Received Date: 30 May 2016
Revised Date: 14 August 2016

Fund Project: the National Natural Sciences Foundation of China 21362008the Undergraduate Innovation and Entrepreneurship Training Program of Henan Province 20140062

Figures(1)

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.
- arylmethyl azides,
- N₂-extrusion,
- aryl aldehydes,
- t-BuOK
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