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



顾君a, 刘建东b, 孙雨人a, 王洪宇b   

  1. 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
  • 基金资助:


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

Gu Juna, Liu Jiandongb, Sun Yurena, Wang Hongyub   

  1. 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
  • 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).

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