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Cyclic Amino(Ylide) Silylene: A Stable Heterocyclic Silylene with Strongly Electron‐Donating Character
Author(s) -
AlvaradoBeltran Isabel,
Baceiredo Antoine,
SaffonMerceron Nathalie,
Branchadell Vicenç,
Kato Tsuyoshi
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609899
Subject(s) - silylene , chemistry , ylide , phosphonium , character (mathematics) , nucleophile , photochemistry , stereochemistry , organic chemistry , catalysis , silicon , geometry , mathematics
An isolable heterocyclic silylene ( 4 ) with two different π‐donating substituents, namely a classical amino group and a more electropositive and stronger carbon‐based π‐donating phosphonium ylide, was synthesized and fully characterized. The combination of these two different π‐donating substituents confers high thermal stability and an unusual nucleophilic character on silylene 4 . Therefore, silylene 4 behaves as a strong donor ligand toward transition metals with a donating character comparable to N ‐heterocyclic carbenes, in contrast to classical N ‐heterocyclic silylenes, which generally present a weak donating character.