217803-12-8Relevant articles and documents
Chalcogen electrophile induced rearrangement of 1-alkynyltrialkyl borates: Controlled syntheses of trisubstituted olefins from 1-alkynes
Gerard, Julien,Hevesi, László
, p. 9109 - 9121 (2007/10/03)
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.