Nickel-Catalyzed Reductive Methylation of Alkyl Acid with Methyl p-Tosylate

doi:10.6023/cjoc201703042

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1830-1834.DOI: 10.6023/cjoc201703042 Previous Articles Next Articles

Notes

镍催化烷基羧酸与对甲苯磺酸甲酯还原偶联甲基化成酮反应

顾君^a, 刘建东^b, 孙雨人^a, 王洪宇^b

a. 上海大学材料科学与工程学院上海 200444;
b. 上海大学理学院化学系上海 200444

收稿日期:2017-03-24 修回日期:2017-04-16 发布日期:2017-05-17
通讯作者: 王洪宇 E-mail:wanghy@shu.edu.cn
基金资助:
国家自然科学基金（No.61204020）和上海市教委创新（No.15ZZ047）资助项目.

Nickel-Catalyzed Reductive Methylation of Alkyl Acid with Methyl p-Tosylate

Gu Jun^a, Liu Jiandong^b, Sun Yuren^a, Wang Hongyu^b

a. School of Materials Science and Engineering, Shanghai University, Shanghai 200444;
b. Department of Chemistry, Shanghai University, Shanghai 200444

Received:2017-03-24 Revised:2017-04-16 Published:2017-05-17
Contact: 10.6023/cjoc201703042 E-mail:wanghy@shu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No.61204020) and the Innovation Program of Shanghai Municipal Education Commission (No.15ZZ047).

1. Nickel-Catalyzed Reductive Methylation of Alkyl Acid with Methyl p-Tosylate.PDF(8008KB)

Abstract

Methyl group is the smallest carbon substituent that plays important roles in many compounds. Conversion of a carboxylic acid into a ketone is a fundamental transformation in organic chemistry. This functional group change is usually performed indirectly by activating the carboxylic acid into an acyl chloride or into a Weinreb amide, and then by nucleophilic attack with an organometallic reagent. However, direct conversion of a carboxylic acid into a ketone can be achieved in one-step reaction using at least 2 equiv. of an organolithium reagent at low temperature and producing much tertiary alcohol. Herein, methylation of alkyl acid under Ni-catalyzed reductive coupling conditions using methyl p-methyl tosylate as the methylation reagent was reported to yield methylated ketones. Moderate yields as well as good functional group tolerance were observed under the present mild and easy-to-operate reaction conditions.

Key words: methylation, nickel-catalyzed, alkyl acid, reductive coupling

Cite this article

Gu Jun, Liu Jiandong, Sun Yuren, Wang Hongyu. Nickel-Catalyzed Reductive Methylation of Alkyl Acid with Methyl p-Tosylate[J]. Chin. J. Org. Chem., 2017, 37(7): 1830-1834.

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镍催化烷基羧酸与对甲苯磺酸甲酯还原偶联甲基化成酮反应

Nickel-Catalyzed Reductive Methylation of Alkyl Acid with Methyl p-Tosylate

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