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Polarity‐Reversal‐Catalyzed Hydrostannylation Reactions: Benzeneselenol‐Mediated Homolytic Hydrostannylation of Electron‐Rich Olefins
Author(s) -
Ford Leigh,
Wille Uta,
Schiesser Carl H.
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690214
Subject(s) - chemistry , homolysis , catalysis , yield (engineering) , styrene , photochemistry , medicinal chemistry , polymer chemistry , radical , organic chemistry , copolymer , polymer , materials science , metallurgy
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.