Photosensitizer-free, visible light-mediated heterogeneous gold-catalyzed cross-coupling of aryldiazonium salts with allyltrimethylsilane

Abstract

An efficient visible light-mediated and heterogeneous gold-catalyzed cross-coupling of aryldiazonium tetrafluoroborates and allyltrimethylsilane has been developed. The photosensitizer-free cross-coupling reaction proceeds smoothly in MeCN under irradiation with blue LEDs at room temperature by using 10 mol% of SBA-15-supported triphenylphosphine-gold(I) complex [SBA-15-Ph₃PAuCl] as catalyst and provides a general and practical route for the synthesis of allylarenes in moderate to good yields. This heterogenized gold(I) catalyst can be readily recovered via a simple filtration of the reaction mixture and recycled up to eight times without any significant loss of catalytic activity.

Graphical Abstract

Keywords:

• Allylarene
• cross-coupling
• Gold
• heterogeneous catalysis
• photoredox catalysis

Additional information

Funding

We thank the National Natural Science Foundation of China (No. 21664008) for financial support.