Coupling of alkynylTMS derivatives with vinylic iodides. An efficient route to 1,3-enynes and dienes.
[reaction: see text] CuCl-promoted coupling of alkynylTMS derivatives with vinyl iodides leads to 1,3-enynes in high yield. Enynes prepared from homopropargylic alcohols undergo intramolecular hydrosilylation and subsequent silyl cleavage with TBAF to afford 1,3-dienes.
Marshall
J A
JA
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA. jam5x@virginia.edu
Chobanian
H R
HR
Yanik
M M
MM
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
D000447:Aldehydes; D000475:Alkenes; D000480:Alkynes; D007454:Iodides; D020005:Propanols; D014753:Vinyl Compounds; C028255:propargyl alcohol