Details

Autor(en) / Beteiligte

• Pan, Decheng
• Pan, Zilong
• Hu, Zhiming
• Li, Meichao
• Hu, Xinquan
• Jin, Liqun
• Sun, Nan
• Hu, Baoxiang
• Shen, Zhenlu

Titel

Metal‐Free Aerobic Oxidative C–O Coupling of C(sp3)–H with Carboxylic Acids Catalyzed by DDQ and tert‐Butyl Nitrite

Ist Teil von

• European journal of organic chemistry, 2019-09, Vol.2019 (33), p.5650-5655

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. A metal‐free aerobic oxidative cross‐coupling reaction between a benzylic C(sp3)–H bond and a carboxylic acid catalyzed by 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone and tert‐butyl nitrite has been developed. This protocol provides a mild and efficient route to obtain diarylmethanol esters and phthalides. It can be regarded as a typical example of green chemistry in oxidative C–O coupling.