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The conjugated dienamine4 selectively adds Piers' borane [HB(C6 F5 )2 ] to give the enamine/borane system5 , which features a boratirane structure by internal enamine carbon Lewis base to boron Lewis acid interaction. Compound5 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’.

philosophical transactions - royal society. mathematical, physical and engineering sciences/philosophical transactions - royal society. mathematical, physical and engineering sciences

Design and reactions of a carbon Lewis base/boron Lewis acid frustrated Lewis pair