Abstract
The conjugated dienamine 4 selectively adds Piers' borane [HB(C6F5)2] to give the enamine/borane system 5, which features a boratirane structure by internal enamine carbon Lewis base to boron Lewis acid interaction. Compound 5 behaves as a C/B frustrated Lewis pair and undergoes typical addition reactions to benzaldehyde, several nitriles and to sulfur dioxide.This article is part of the themed issue 'Frustrated Lewis pair chemistry'.
Highlights
Frustrated Lewis pairs (FLPs) undergo cooperative reactions with a variety of small molecules [1,2,3]
FLPs are composed of Lewis acid/base pairs which are effectively hindered from neutralizing Lewis adduct formation
Substrates containing the group 15 heteroatoms have taken a dual role in the catalytic hydrogenation process, namely as the reagent rsta.royalsocietypublishing.org Phil
Summary
Frustrated Lewis pairs (FLPs) undergo cooperative reactions with a variety of small molecules [1,2,3]. Most notably, they often split dihydrogen [4,5,6], and many FLPs were shown to selectively add to a variety of organic and inorganic π-systems. FLPs are composed of Lewis acid/base pairs which are effectively hindered (often in an equilibrium situation) from neutralizing Lewis adduct formation. This is mostly done by attaching very bulky substituents at both the Lewis acid and the Lewis base component of the pair. Substrates containing the group 15 heteroatoms have taken a dual role in the catalytic hydrogenation process, namely as the reagent
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