Citation: Gu Jun, Liu Jiandong, Sun Yuren, Wang Hongyu. Nickel-Catalyzed Reductive Methylation of Alkyl Acid with Methyl p-Tosylate[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1830-1834. doi: 10.6023/cjoc201703042 shu

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

Corresponding author: Wang Hongyu, wanghy@shu.edu.cn
Received Date: 24 March 2017
Revised Date: 16 April 2017
Available Online: 17 July 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 61204020) and the Innovation Program of Shanghai Municipal Education Commission (No. 15ZZ047)the Innovation Program of Shanghai Municipal Education Commission 15ZZ047the National Natural Science Foundation of China 61204020

Figures(2)

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.
- methylation,
- nickel-catalyzed,
- alkyl acid,
- reductive coupling
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