Cu‐catalyzed coupling of arylsulfinic salts with arylsilanes under mild conditions

Abstract

Arylsilanes were efficiently coupled with arylsulfinic salts for the first time under mild conditions. Diarylsulfone derivatives were easily synthesized in high yields with the assistance of nitrogen‐containing ligands and KF. The transformation is simple and efficient and the starting materials are readily available. Copyright © 2014 John Wiley & Sons, Ltd.

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…251 In 2014, Yang and co-workers rstly introduced arylsilanes for the copper-catalyzed cross-coupling with sodium arene-sulnates for the synthesis of diaryl sulfones (Table 16; entry-7). 252 The reaction scope was proved with respect to various arylsilanes and different arylsulnates to afford the diaryl sulfones in good to high yields. In 2016, the Shekhar group examined aryltriates for cross-coupling with sodium tri-uoromethanesulnate.…”

Transition‐Metal‐Free Cross‐Coupling of Arylsilanes with DAST Reagent: Synthesis of Aromatic Sulfinamides

“…Organosilanes, especially aryl siloxanes, have drawn continuous attention due to their tractability, high stability, and easy preparation advantages. [11] In 2014, Hou group developed the copper(I)-catalyzed coupling of arylsulfinic salts and arylsilanes (Scheme 1a); [12] Whereafter, Wang group accomplished a three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines catalyzed by copper(II) acetate (Scheme 1b). [13] In 2016, Wu group developed a copper(I)catalyzed three-component reaction of triethoxysilanes, DAB-CO⋅(SO 2 ) 2 , and alkyl halides; Moreover, a cobalt-promoted coupling reaction of triethoxysilanes, sulfur dioxide, and electrophiles (benzylic, allylic or alkyl bromides) was reported (Scheme 1c).…”

“…Under argon atmosphere, the desired product 3 a was obtained in 68% yield ( Table 1, entry 11). Subsequently, various solvents were screened (Table 1, entries [12][13][14], but all of them were found to be less effective than dichloromethane (DCM). Increasing the amount of base to 2.5 equiv.…”