Temperature-controlled NaI-mediated α-oxybenzoylation or oxyacylation–decarboxylation reactions of dimethyl malonate with carboxylic acids

• Published in: Catalysis communications Vol. 70; pp. 62 - 65
• Main Authors: Mao, Jincheng, Liu, Defu, Li, Yongming, Zhao, Jinzhou, Rong, Guangwei, Yan, Hong, Zhang, Guoqi
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.10.2015
• Subjects: Carboxylic acids; Dimethyl malonate; Oxidative decarboxylative; Temperature-controlled; α-Oxybenzoylation; Temperature-controlled; α-Oxybenzoylation; Carboxylic acids; Dimethyl malonate; Oxidative decarboxylative
• ISSN: 1566-7367; 1873-3905
• DOI: 10.1016/j.catcom.2015.07.013

A NaI-mediated α-functionalization of dimethyl malonate and its derivatives with carboxylic acids has been developed. Two different reaction routes based on the same substrates and reaction conditions by simply altering the reaction temperature have been observed, which led to the synthesis of two types of products in good to high yields. The scope of substrates was investigated for both types of reactions, respectively, and possible reaction mechanisms were suggested. A NaI-mediated α-functionalization of dimethyl malonate and its derivatives with carboxylic acids has been developed. Two different reaction routes based on the same substrates and reaction conditions by simply altering the reaction temperature have been observed, which led to the synthesis of two types of products in good to high yields. The scope of substrates was investigated for both types of reactions, respectively, and possible reaction mechanisms were suggested. [Display omitted] •NaI-mediated α-oxybenzoylation of dimethyl malonate with carboxylic acids was developed.•Two different reaction routes controlled by temperature were observed.•Two types of coupling products were isolated in good to high yields.•The reaction mechanisms were proposed based on the results observed.