Synthesis of α-arylalkylferrocenes through cesium fluoride-promoted coupling of arylboronic acids with N-tosylhydrazones

ABSTRACT

A cesium fluoride-promoted reductive coupling reaction of acylferrocene tosylhydrazones with arylboronic acids has been developed, producing highly substituted α-arylalkylferrocenes in moderate to excellent yields. The reaction employs anionic fluorine to facilitate the cleavage of C–B bond. The developed methodology demonstrates a wide substrate scope and high functional groups tolerance. Moreover, the α-arylalkylferrocenes compounds were also obtained on a multi-gram scale.

GRAPHICAL ABSTRACT

KEYWORDS:

• α-Arylalkylferrocene
• Boronic acid
• synthesis
• tosylhydrazones

Additional information

Funding

We gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (No. 21563025), Shihezi University Training Programme for Distinguished Youth Scholars (No. 2014ZRKXJQ05), Start-Up Foundation for Young Scientists of Shihezi University (RCZX201408), and the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT_15R46), and Yangtze River scholar research project of Shihezi University (No. CJXZ201601).