Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Exceptionally Strong Electron-Donating Ability of Bora-Ylide Substituent vis-à-vis Silylene and Silylium Ion

Exceptionally Strong Electron-Donating Ability of Bora-Ylide Substituent vis-à-vis Silylene and Silylium Ion
Vicenç Branchadell, Stéphane Massou, Tsuyoshi Kato, Isabel Alvarado-Beltran, Nathalie Saffon-Merceron, Alfredo Rosas-Sánchez, Antoine Baceiredo
Electropositive boron-based substituent (phosphonium bora-ylide) with an exceptionally strong π- and σ-electron donating character dramatically increases the stability of a new type of N-heterocyclic silylene 2 featuring amino- and bora-ylide-substituents. Moreover, the related silylium ion 4 and transition-metal–silylene complexes, with trigonal-planar geometries around the silicon center, are also well stabilized. Therefore, the N,B-heterocyclic silylene 2 can be used as a strongly electron-donating innocent ligand in coordination chemistry similarly to N-heterocyclic carbenes. Electron-donating ligand: An electropositive boron-based substituent (phosphonium bora-ylide) with an exceptionally strong π- and σ-electron donating character increases the stability a new type of N-heterocyclic silylene featuring amino and bora-ylide substituents. It also efficiently stabilizes the related silylium ion and transition-metal–silylene complexes even with a trigonal-planar geometry around the silicon center.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201705302

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