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N‐Heterocyclic Silylenes in Boron Chemistry: Facile Formation of Silylboranes and Silaborinines
Author(s) -
Gackstatter Annika,
Braunschweig Holger,
Kupfer Thomas,
Voigt Christian,
Arnold Nicole
Publication year - 2016
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.201603945
Subject(s) - silylene , borane , chemistry , boron , steric effects , ring (chemistry) , sequence (biology) , computational chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , silicon , biochemistry
Reaction of a N‐heterocyclic silylene (NHSi) with PhBX 2 (X=Cl, Br) readily afforded six‐membered silaborinines through an insertion/ring expansion sequence. Increasing the sterics of the borane from phenyl to duryl enabled the selective generation and isolation of the highly colored silylborane intermediates. Theoretical studies on the mechanism and energetics of the silaborinine formation were fully consistent with the experimental observations.