Room-temperature Stille cross-couplings of alkenyltin reagents and functionalized alkyl bromides that possess beta hydrogens.
This communication describes a significant expansion in the scope of Stille reactions of Csp3-X electrophiles, specifically, that Pd/P(t-Bu)2Me catalyzes the room-temperature cross-coupling of a variety of functionalized, beta-hydrogen-containing alkyl bromides with an array of alkenyltin reagents. The structure of the phosphine (P(t-Bu)2Me) is well suited for facilitating oxidative addition and avoiding beta-hydride elimination, while the fluoride serves to activate the tin reagent for efficient transmetalation.
Menzel
Karsten
K
Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139, USA.
Fu
Gregory C
GC
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013696:Temperature; D014001:Tin / Q000737:chemistry*
D000475:Alkenes; D006842:Hydrocarbons, Brominated; D009942:Organometallic Compounds; D010165:Palladium; D014001:Tin; D006859:Hydrogen