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.

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