Reduction of Sulfoxides to Sulfides in the Presence of Copper Catalysts

Abstract

Copper complexes catalyze the reduction of aliphatic and aromatic sulfoxides in the presence of silanes as reducing reagent. The influence of different reaction parameters on the catalytic activity is investigated in detail. The scope and limitations of the described catalyst is demonstrated in the reduction of various sulfoxides. In most cases, high conversion and excellent chemoselectivity are obtained.

A polymer analogous reaction for the formation of imidazolium and NHC based porous polymer networks

“…[52][53][54] Recently, the copper-catalyzed deoxygenation of sulfoxides applying hydrosilanes as reductant has been demonstrated. 55,56 As pre-catalysts Cu(acac) 2 has been proven to obtain the desired products in excellent yields and selectivities. 55 However, the application of copper salts as pre-catalysts allows not for an easy separation and in consequence not for a recycling of the catalyst.…”

“…55,56 As pre-catalysts Cu(acac) 2 has been proven to obtain the desired products in excellent yields and selectivities. 55 However, the application of copper salts as pre-catalysts allows not for an easy separation and in consequence not for a recycling of the catalyst. In this regard the utilization of the Cu-coordinated network (PCu-NHC) can be a recyclable alternative.…”

Copper-Catalyzed Dehydration of Primary Amides to Nitriles

“…As the dehydration of primary amides is proposed to proceed via silylation we wonder if the hydrosilanes can be replaced by silylation reagents to avoid additional reduction [25,27,28]. In accordance to that we herein present the efficient application of copper precursors in combination with N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) in the dehydration of a variety of primary amides to yield the corresponding nitriles [29].…”

Synthesis of δ- and ε-Cyanoesters by Zinc-Catalyzed Ring-Opening of Cyclic Ethers with Acid Chlorides and Subsequent Cyanation

“…Herein we present based on our ongoing interest in zincchemistry an efficient and straightforward two step protocol based on zinc-catalyzed ring opening of cyclic ethers and subsequent cyanation to access protected hydroxynitriles with tunable chain length [30][31][32][33][34][35][36].…”