98204-60-5

Upstream product

• 30089-00-0 9-octyl-9-bora-bicyclo[3.3.1]nonane 
• 80485-53-6 phenyl α-bromovinyl sulfide 
• 764-93-2 1-decyne 
• 113034-93-8 9-(phenylthio)-9-borabicyclo<3.3.1>nonane 
• 54532-96-6 Ethyl 2-phenylthiodecanoate 
• 408327-58-2 2-Phenylsulfanyl-decan-1-ol 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 98204-58-1 3-Octyl-1-oxa-4-thia-spiro[4.5]decane 

Downstream Products

• 115993-67-4 2-Methyl-2-phenylsulfanyl-decanenitrile 
• 106918-90-5 2-(1-Methyl-1-phenylsulfanyl-nonyl)-cyclohexanone 
• 108162-73-8 1-(2-Octyl-2-phenylsulfanyl-cyclobutyl)-ethanone 
• 121033-28-1 1-(phenylthio)-2-decanone 
• 115993-74-3 (1-Allyl-1-methyl-nonylsulfanyl)-benzene 
• 108162-80-7 1-(2-Benzenesulfonyl-2-octyl-cyclobutyl)-ethanone 

Relevant academic research and scientific papers

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.

A STEREOSELECTIVE ROUTE TO ALKENYL SULFIDES THROUGH THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 9-ALKYL-9-BBN WITH 1-BROMO-1-PHENYLTHIOETHENE OR (E)- AND (Z)-2-BROMO-1-PHENYLTHIO-1-ALKENES

The reaction of 9-alkyl-9-BBNs with 1-bromo-1-phenylthioethene or (E)- and (Z)-2-bromo-1-phenylthio-1-alkenes takes place readily in the presence of Pd(PPh3)4 and sodium hydroxide to afford stereodefined vinylic sulfides in exellent yields.

BENZYNE-INDUCED FRAGMENTATION OF 1,3-OXATHIOLANES. A NOVEL METHOD FOR DEPROTECTION OF CARBONYL GROUPS, PREPARATION OF PHENYL VINYL SULFIDES, AND 1,2-CARBONYL TRANSPOSITION

A variety of 1,3-oxathiolanes undergo a benzyne-induced fragmentation leading to phenyl vinyl sulfides and carbonyl compounds.The reaction developed here provides a novel method for deprotection of carbonyl compounds from 1,3-oxathiolanes, preparation of phenyl vinyl sulfides, and 1,2-carbonyl transposition.