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Nucleophilic Silylenoid Character of Stable Phosphonium Sila–ylides
Author(s) -
Gau David,
Rodriguez Ricardo,
Kato Tsuyoshi,
SaffonMerceron Nathalie,
Cossío Fernando P.,
Baceiredo Antoine
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001054
Subject(s) - phosphonium , nucleophile , cycloaddition , chemistry , adduct , silylene , phosphine , medicinal chemistry , organic chemistry , silicon , catalysis
Stabilising the core : Contrary to the case of non‐stabilised transient silylenes, which react with carbonyl compounds to form donor–acceptor adducts, the reaction of a phosphine‐coordinated silylene with an aldehyde proceeds by a concerted [2+1] cycloaddition with a very low energy barrier to afford a pentacoordinate oxasilirane (see scheme). This result clearly demonstrates the behaviour of phosphonium sila–ylides as nucleophilic silylenoids.