A simple and efficient synthesis of 9-arylfluorenes via metal-free reductive coupling of arylboronic acids and N-tosylhydrazones in situ

作者：Shen, Xu; Gu, Ningning; Liu, Ping^*; Ma, Xiaowei; Xie, Jianwei; Liu, Yan; He, Lin; Dai, Bin

来源：RSC Advances, 2015, 5(78): 63726-63731.

DOI：10.1039/c5ra12099c

• TERMINAL ALKYNES
• CARBONYL-COMPOUNDS
• ALKYLATION
• ROUTE
• GENERATION
• YLIDES
• DIAZOESTERS
• DERIVATIVES
• THIOPHENE
• ARYLATION

A general, yet efficient synthesis method of 9-arylfluorenes via metal-free reductive coupling of N-tosylhydrazones and arylboronic acids has been developed. This methodology is realized by a one-pot protocol in two steps involving the preparation of N-tosylhydrazones by reacting tosylhydrazide with 9-fluorenone derivatives, followed by the reductive coupling of arylboronic acid in the presence of potassium carbonate to afford various 9-arylfluorenes analogues in moderate to excellent yields. Importantly, the catalytic system presented here enables the use of easily accessible starting materials and can be employed on a wide variety of substrates with good functional group tolerance. This protocol could also be particularly useful for the synthesis of 9-fluorenyl-substituted carbazolyl compounds.

• 出版日期2015
• 单位石河子大学