Copper-Promoted Cross-Coupling Reactions for the Synthesis of Aryl(difluoromethyl)phosphonates Using Trimethylsilyl(difluoromethyl)phosphonate

Kazuki Komoda; Rei Iwamoto; Masakazu Kasumi; Hideki Amii

doi:10.3390/molecules23123292

Copper-Promoted Cross-Coupling Reactions for the Synthesis of Aryl(difluoromethyl)phosphonates Using Trimethylsilyl(difluoromethyl)phosphonate

Molecules. 2018 Dec 11;23(12):3292. doi: 10.3390/molecules23123292.

Authors

Kazuki Komoda¹, Rei Iwamoto², Masakazu Kasumi³, Hideki Amii⁴

Affiliations

¹ Division of Molecular Science, Graduate School of Science and Technology, 1-5-1, Tenjin-cho, Kiryu, Gunma 376-8515, Japan. t162a004@gunma-u.ac.jp.
² Department of Chemistry, Graduate School of Science, Kobe University, Nada-ku, Kobe 657-8501, Japan. qq5f25s9n@energy.ocn.ne.jp.
³ Division of Molecular Science, Graduate School of Science and Technology, 1-5-1, Tenjin-cho, Kiryu, Gunma 376-8515, Japan. t11801125@gunma-u.ac.jp.
⁴ Division of Molecular Science, Graduate School of Science and Technology, 1-5-1, Tenjin-cho, Kiryu, Gunma 376-8515, Japan. amii@gunma-u.ac.jp.

Abstract

A convenient and effective route for the synthesis of aryl(difluoromethyl)phosphonates has been developed based on cross-coupling reactions. Upon treatment with a stoichiometric amount (or a catalytic amount in some cases) of CuI and CsF, aryl iodides reacted smoothly with (silyldifluoromethyl)phosphonates to give the corresponding aryl(difluoromethyl)phosphonates in good yields.

Keywords: copper; cross-coupling; difluoromethyl; phosphonates; silicon.

MeSH terms

Chemistry Techniques, Synthetic
Copper / chemistry*
Iodides / chemistry
Organophosphonates / chemical synthesis*
Organophosphonates / chemistry

Substances

Iodides
Organophosphonates
Copper