Cyclic Amino(Ylide) Silylene: A Stable Heterocyclic Silylene with Strongly Electron‐Donating Character. (25th November 2016)

• Record Type: Journal Article
• Authors: Alvarado‐Beltran, Isabel; Baceiredo, Antoine; Saffon‐Merceron, Nathalie; Branchadell, Vicenç; Kato, Tsuyoshi
• Is Part Of: Angewandte Chemie. Volume 128:Number 52(2016)
• Page Start: 16375
• Page End: 16378
• Publication Date: 2016-11-25
• Subjects: Hauptgruppenchemie -- Heterocyclen -- Ligandeneffekte -- Ligandenentwicklung -- Silylene; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201609899
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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 silylene4 . Therefore, silylene4 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.