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Seven- and eight-membered heterocyclic biaryl synthesis through a metal-free oxidative coupling reaction
Affiliation:1. Department of Natural Product Chemistry, Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China;2. Department of Pharmaceutical Analysis, School of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, China;3. Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University), Ministry of Education of China, Guilin 541004, China;1. Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, Jinan, 250012, China;2. School of Pharmacy, Liaocheng University, Liaocheng, China;3. School of Pharmacy and Medical Sciences, University of South Australia, Adelaide, SA, 5000, Australia;4. Department of Medical Laboratory, College of Applied Medical Sciences–Shaqra, Shaqra University, 11961, Saudi Arabia
Abstract:A metal-free intramolecular biaryl coupling mediated by DDQ and BF3·OEt2 was developed. The reaction proceeds smoothly at room temperature to give seven- and eight-membered heterocyclic biaryl compounds in up to 95% yields. Only 1 equiv of DDQ sufficed for the reaction, obviating the use of a large excess of oxidants and undesired chlorination pathway in metal-mediated process.
Keywords:Biaryl coupling  Intramolecular  Metal-free  Heterocyclic  Seven- and eight-membered ring
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