AgF-Mediated Homocoupling Reaction of Trialkoxy Aryl Silanes

Abstract

In this article, we present the direct homocoupling reaction of trialkoxy aryl silanes mediated by AgF in moderate to excellent yields in very mild conditions. It is an important complement for the synthesis of symmetrical biaryls by using homocoupling of trialkoxy silanes. In this reaction, no other catalyst such as Pd or Cu was necessary.

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GRAPHICAL ABSTRACT

Keywords:

• Ag-mediated
• biaryls
• homocoupling
• N,N-dimethylformamide
• phenyltrimethoxysilane

ACKNOWLEDGMENTS

This project was supported by the Natural Science Foundation of Jiangxi, China (No. 2008GZH0014). The authors aslo thank Gannan Normal University for financial support.

Notes

^a Reactions were carried out with 1.05 equiv of fluoride, 2.0 mL solvent, 8 h.

^b Isolated yield based on phenyltrimethoxysilane.

^c TBAF = tetra-n-butylammonium fluoride.

^d 10 mol% PdCl₂ and 2.0 equiv TBAF.

^e 10 mol% CuCl or CuI and 1.1 equiv TBAF.

^f 0.5 equiv AgF was used.

^g 1.0 equiv AgF was used.

^h 1.4 equiv AgF was used.

ⁱ Using phenyltriethoxysilane as substrate.

^a Reactions were carried out with 1.05 equiv of silver fluoride, 2.0 mL DMF.

^b Isolated yield based on trialkoxy aryl silanes.