Palladium-Catalyzed Direct Acyloxylation of C (sp2)—H and C (sp3)—H Bonds under the Assistance of Oxalyl Amide

doi:10.6023/cjoc201701032

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2066-2072.DOI: 10.6023/cjoc201701032 Previous Articles Next Articles

ARTICLE

草酰胺导向下钯催化的C(sp²)—H和C(sp³)—H键的直接酰氧基化反应

郑永祥, 韩健, 黄志斌, 史达清, 赵应声

苏州大学材料与化学化工学部苏州 215123

收稿日期:2017-01-16 修回日期:2017-03-22 发布日期:2017-04-13
通讯作者: 史达清, 赵应声 E-mail:dqshi@suda.edu.cn;yszhao@suda.edu.cn
基金资助:
国家自然科学基金（Nos.21403148，21572149）和江苏省高校自然科学重大研究（No.15KJA150006）资助项目.

Palladium-Catalyzed Direct Acyloxylation of C (sp²)—H and C (sp³)—H Bonds under the Assistance of Oxalyl Amide

Zheng Yongxiang, Han Jian, Huang Zhibin, Shi Daqing, Zhao Yingsheng

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received:2017-01-16 Revised:2017-03-22 Published:2017-04-13
Contact: 10.6023/cjoc201701032 E-mail:dqshi@suda.edu.cn;yszhao@suda.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21403148, 21572149) and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 15KJA150006).

1. Palladium-Catalyzed Direct Acyloxylation of C (sp²)—H and C (sp³)—H Bonds under the Assistance of Oxalyl Amide.PDF(1537KB)

Abstract

A practical palladium-catalyzed direct acyloxylation of C(sp²)—H and C(sp³)—H bonds under the assistance of oxalyl amide with TBPB as oxidant was developed. Selective acyloxylation of C(sp²)—H bond for oxalyl amide protected benzyl amine using TBPB or carboxylic acids as acyloxylating reagent was achieved. For oxalyl amide protected 2-alkylanilines, the selective acyloxylation of benzylic C(sp³)—H bond was also achieved. This protocol provided an efficient and practical method for the synthesis of aryl esters.

Key words: acyloxylation, C(sp²)—H bond, C(sp³)—H bond

Cite this article

Zheng Yongxiang, Han Jian, Huang Zhibin, Shi Daqing, Zhao Yingsheng. Palladium-Catalyzed Direct Acyloxylation of C (sp²)—H and C (sp³)—H Bonds under the Assistance of Oxalyl Amide[J]. Chin. J. Org. Chem., 2017, 37(8): 2066-2072.

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草酰胺导向下钯催化的C(sp²)—H和C(sp³)—H键的直接酰氧基化反应

Palladium-Catalyzed Direct Acyloxylation of C (sp²)—H and C (sp³)—H Bonds under the Assistance of Oxalyl Amide

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草酰胺导向下钯催化的C(sp2)—H和C(sp3)—H键的直接酰氧基化反应