✦ LIBER ✦
Polarity-Reversal-Catalyzed Hydrostannylation Reactions: Benzeneselenol-Mediated Homolytic Hydrostannylation of Electron-Rich Olefins
✍ Scribed by Leigh Ford; Uta Wille; Carl H. Schiesser
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- German
- Weight
- 65 KB
- Volume
- 89
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Addition of 10 mol‐% of diphenyl diselenide to 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 benefits, by the increased rate of H‐atom transfer, from the in situ generated polarity‐reversal catalyst, benzeneselenol.