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

doi:10.1039/C5RA12099C

Paper

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

Published Jul 22, 2015 · Xu Shen, N. Gu, Ping Liu

RSC Advances

24

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0

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Abstract

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.

Study Snapshot

This study developed a simple, efficient method for synthesis of 9-arylfluorenes using metal-free reductive coupling of N-tosylhydrazones and arylboronic acids, offering moderate to excellent yields and good functional group tolerance.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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