Diversity-oriented synthesis of disubstituted alkenes using masked silanols.
The regio- and stereoselective synthesis and subsequent Hiyama cross coupling of pentafluorophenyldimethylvinylsilanes has been developed, thus providing a convenient and robust method for the diversity-oriented synthesis of (E)-, (Z)- and alpha-disubstituted alkenes from terminal alkynes. Pentafluorophenyldimethylvinylsilanes undergo cross-coupling reactions with excellent selectivity and in good yields, offering an attractive alternative to existing masked silanols.
Sore
Hannah F
HF
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.
Blackwell
David T
DT
Macdonald
Simon J F
SJ
Spring
David R
DR
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D006845:Hydrocarbons, Fluorinated; D012821:Silanes; C082343:silanol