A palladium-catalyzed carbothiolation via the reaction of a σ-alkyl palladium intermediate with a TIPS thioether is described. It was found that the use of Cs 2 CO 3 , (IPr)Pd(allyl)Cl, and a TIPS thioether was key to obtaining alkyl aryl and dialkyl sulfides in high yield through the reaction of a σ-alkyl palladium intermediate. The developed reaction is applicable to a wide range of substrates and thiols.
Herein, we describe a palladium-catalyzed thiocarbonylation via the reaction of a σ-alkyl palladium intermediate with carbon monoxide (CO) and a TIPS thioether. The use of CsF, (IPr)Pd(allyl)Cl, CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depends on the structure of substrate and it was observed that indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with PhSTIPS and CsF were also demonstrated to form the corresponding thioesters.
A palladium-catalyzed cascade reaction for preparing 2,3-dihydrobenzo[b]thiophenes and the corresponding 1,1-dioxides bearing the C3 benzylic quaternary carbon is described. This cascade reaction involves the oxidative addition of aryl iodide to Pd(0) to form a σ-aryl palladium intermediate,
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