661488-99-9

Upstream product

• 122-56-5 tributyl borane 
• 693-02-7 hex-1-yne 
• 931-59-9 benzenesulfenyl chloride 
• 42126-47-6 C₁₈H₃₆B^(1-)*Li⁽¹⁺⁾ 

Downstream Products

• 661489-01-6 (Z)-5-benzyl-6-(phenylthio)-5-decene 
• 110897-35-3 5-phenyl-(Z)-5-decene 
• 66619-22-5 (E)-(1-butyl-hex-1-enyl)-benzene 
• 92-52-4 biphenyl 
• 661489-00-5 (E)-5-methyl-6-(phenylthio)-5-decene 
• 1942-46-7 5-decyne 
• 622-38-8 Ethyl phenyl sulfide 
• 137298-83-0 (E)-5-(phenylthio)dec-5-ene 
• 137298-82-9 (Z)-5-(phenylthio)dec-5-ene 

Relevant academic research and scientific papers

Transformation of β-chalcogeno alkenylboranes into tetrasubstituted olefins

In view of generating trisubstituted vinylic chalcogen derivatives, β-chalcogeno alkenylboranes generated through the chalcogen electrophile induced rearrangements of 1-alkynyltrialkyl borates have been subjected to Suzuki-Miyaura coupling and to boron to copper transmetalation followed by alkylation. Some of the trisubstituted vinyl sulfides obtained by this latter strategy have been converted efficiently into the title olefins through the NiCl2(dmpe) catalyzed coupling with various Grignard reagents.

Chalcogen electrophile induced rearrangement of 1-alkynyltrialkyl borates: Controlled syntheses of trisubstituted olefins from 1-alkynes

The reaction of 1-alkynyltrialkyl borates with sulfenyl, selenenyl and tellurenyl halides produces β-chalcogeno alkenylboranes in good yields, with a cis relationship between the boron and the chalcogen moities. Protodeborylation of these compounds by acetic acid, or by a transmetalation-protonolysis sequence, leads to vinyl chalcogenides, which can be converted to alkenes by means of a nickel catalyzed coupling with Grignard reagents. Since the last two steps occur with retention of the stereochemistry, the overall sequence represents a highly regio- and stereoselective olefin synthesis.