A facile route to vinyl- and arylphosphonates by vinyl and aryl radical trapping with (MeO)3P.
The generation of vinyl or aryl radicals under classical, thermal AIBN/n-Bu(3)SnH conditions at 80 degrees C in the presence of an excess of (MeO)(3)P gives rise to the corresponding vinyl- or arylphosphonates in good yields. This approach complements the photochemical reactions of the same systems previously used. Reactions with the individual stereoisomers of MeCH=CHMeBr (thermal AIBN/n-Bu(3)SnH conditions) afford a radical-equilibrated 96/4 E/Z ratio of vinylphosphonates. Substitution of (TMS)(3)SiH for n-Bu(3)SnH yields an approximately 1/1 ratio of separable E and Z vinylphosphonate diastereomers.
Jiao
Xian-Yun
XY
Department of Chemistry, University of Utah, Salt Lake City, UT 84112, USA.
Bentrude
Wesley G
WG
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007202:Indicators and Reagents; D015394:Molecular Structure; D063065:Organophosphonates / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D014753:Vinyl Compounds / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D063065:Organophosphonates; D014753:Vinyl Compounds