138904-91-3

Upstream product

• 108-86-1 bromobenzene 
• 113034-93-8 9-(phenylthio)-9-borabicyclo<3.3.1>nonane 
• 693-02-7 hex-1-yne 
• 591-50-4 iodobenzene 
• 109-72-8 n-butyllithium 
• 259669-67-5 (Z)-1-(phenylsulphenyl)-2-phenylethenyl p-toluenesulfonate 
• 35460-31-2 (2-phenylsulfanylethynyl)benzene 

Downstream Products

• 25870-62-6 1-phenyl-2-hexanone 

Relevant academic research and scientific papers

Stereoselective synthesis of (Z)-α-organothiovinyltosylates and their application in the synthesis of highly functionalized vinylic sulfides

Thioacetylenes 1 afford, upon treatment with p-toluenesulfonic acid in dichloromethane, (O,S)-ketene acetals 2 which can act as useful α-(organothio)vinyl carbocation equivalents, opening a novel route to functionalized vinylic sulfides.

Palladium(0)-catalyzed thioboration of terminal alkynes with 9-(alkylthio)-9-borabicyclo[3.3.1]nonane derivatives: Stereoselective synthesis of vinyl sulfides via the thioboration-cross-coupling sequence

Theaddition of 9-(alkylthio)-9-borabicyclo[3.3.1]nonanes(9-(RS)-9-BBN) 1 to terminal alkynes was catalyzed by Pd(PPh3)4 (3 mol %) to produce 9-[(Z)-2-(alkylthio)-1-alkenyl]-9-BBN derivatives 2 in high yields. The reactions were highly regio- and stereoselective, and their conditions were sufficiently mild that a variety of functionalized alkenylboranes 2 with defined stereochemistry were readily synthesized. The boranes 2 exhibited exceptionally high reactivity on protonolysis with methanol to produce the Markovnikov adducts of thiols to 1-alkynes, 2-(alkylthio)-1-alkenes 3. The synthetic utility of the present reaction was demonstrated by the regio- and stereoselective one-pot synthesis of alkenyl sulfides 7 via the palladium-catalyzed thioboration-cross-coupling sequence.