217803-17-3Relevant academic research and scientific papers
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.
Vinylborane and vinyichalcogenide mediated syntheses of tri- and tetrasubstituted olefins from 1-alkynes
Gerard, Julien,Bietlot, Emerance,Hevesi, Laszlo
, p. 8735 - 8738 (2007/10/03)
The title olefins have been prepared with high regio- and stereocontrol from 1-alkynes through vinyl boranes 1 vinyl chalcogenides; the reaction sequences involved protonolysis or transmetallation - alkylation of the boranes followed by an Ni(0) catalyzed coupling reaction.
