Nickel‐Catalyzed Carbon‐Sulfur Bond Formation through Couplings of Aryl Iodides and Aryl Ethanethioates

Abstract

A nickel‐catalyzed reductive coupling between aryl iodides and aryl ethanethioates has been developed to afford diaryl sulfides. This method provides a novel and practical route to aryl thioetherification and can be effectively applied to electronically diverse aryl iodides without expensive metals such as palladium and ruthenium.

Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage

“…Unfortunately, this one-pot protocol for the formation of S-thioesters was unsuccessful with S-aryl ethanethioates as substrates as used in our previous work. 20…”

Nickel‐Catalyzed Thiocarbonylation of Aryl Iodides with Dialkyl Disulfides for the Synthesis of Thioesters

“…In the same year, Wu et al also reported a thiocarbonylation of arylboronic acids with sulfonyl chlorides for the synthesis of thioesters by nickel catalyst (Scheme 1c) [13c] . Inspired by these works, herein we disclose a three‐component nickel‐catalyzed carbonylation reaction of aryl iodides with disulfides under CO‐gas‐free conditions to produce the thioesters as our continued studies on nickel‐catalyzed C−S bond formation or cleavage [14a–b] . (Scheme 1d).…”

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

“…720 Aryl iodides with electron-donating substituents produce high yields in the reaction with arylthioacetates catalyzed by Ni(II)/bpy in the presence of Zn (Scheme 206, A). 721 Aryl iodides with p-NO 2 or p-CN groups do not react.…”