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- Title
Metal‐Free Aerobic Oxidative C–O Coupling of C(sp<sup>3</sup>)–H with Carboxylic Acids Catalyzed by DDQ and tert‐Butyl Nitrite.
- Authors
Pan, Decheng; Pan, Zilong; Hu, Zhiming; Li, Meichao; Hu, Xinquan; Jin, Liqun; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu
- Abstract
The formation of the C–O bond is one of the hot topics in the area of C(sp3)–H bond functionalization. A metal‐free oxidative cross‐coupling between benzylic C(sp3)–H bond and carboxylic acids has been developed. The reactions were performed with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) as the catalyst, tert‐butyl nitrite (TBN) as the co‐catalyst, and molecular oxygen as the terminal oxidant. A variety of diarylmethanes could be successfully coupled with various carboxylic acids to obtain diarylmethanol esters in good to excellent yields. In addition, 2‐benzylbenzoic acids could be converted into phthalides in moderate yields through an intramolecular oxidative cyclization.
- Subjects
CARBOXYLIC acids; OXIDATIVE coupling; NITRITES; ESTERS; OXIDIZING agents; OXYGEN
- Publication
European Journal of Organic Chemistry, 2019, Vol 2019, Issue 33, p5650
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201900773