Polarity-Reversal-Catalyzed Hydrostannylation Reactions: Benzeneselenol-Mediated Homolytic Hydrostannylation of Electron-Rich Olefins
作者:Leigh Ford、Uta Wille、Carl H. Schiesser
DOI:10.1002/hlca.200690214
日期:2006.10
hydrostannylation reactions involving electron-rich olefins results in a dramatic improvement in yield. For example, reaction of α-[(tert-butyl)dimethylsilyl]oxy}styrene (1) with triphenylstannane (2a; 1.1 equiv.) in the presence of PhSeSePh and 2,2′-azobis[2-methylpropanenitrile] (AIBN) affords 2-[(tert-butyl)dimethylsilyl]oxy}-2-phenylethyl}triphenylstannane (3a) in 95% yield after 2 h. This reaction presumably
Synthesis and Spectral Studies (FT‐IR,<sup>1</sup>H,<sup>13</sup>C,<sup>119</sup>Sn, and Mass Spectrometry) of Mixed Organotin(IV) Compounds Containing a Long Chain Alkyl Group (<i>n</i>‐C<sub>7</sub>H<sub>15</sub>)
作者:Saqib Ali、Amin Badshah
DOI:10.1081/sim-120030432
日期:2004.3
Franco, G. J. del; Resenick, P.; Dillard, C. R., Journal of Organometallic Chemistry, 1965, vol. 4, p. 57 - 66
作者:Franco, G. J. del、Resenick, P.、Dillard, C. R.
DOI:——
日期:——
Free Radical Hydrostannylation of Unactivated Alkenes with Chiral Trialkylstannanes
作者:Yvonne Kavanagh、Leigh Ford、Carl H. Schiesser
DOI:10.1021/om200473c
日期:2011.8.22
Free radical hydrostannylation of olefins with differing steric and electronic demands have been carried out using the chiral, nonracemic stannanes (1R,2S,5R)-menthyldiphenyltin hydride (7), bis[(1R,2S,5R)-menthyl]phenyltin hydride (8), and tris[(1R,2S,5R)-menthyl]tin hydride (9). These reactions resulted in adducts 16-18 with yields that were found to depend on the nature of the substituents on both alkene and stannane and could be carried out at low temperature initiated by triethylborane and oxygen; MenPh(2)SnH (7) reacted with tert-butyldimethyl(1-phenylvinyloxy)silane (1) at -78 degrees C to afford adduct 19 in near-quantitative yield. Somewhat surprisingly, addition of small quantities of diphenyl diselenide to these reactions failed to improve the outcome under any circumstances.