Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles: - -aryl--nucleophilic substitution

Herein we report two different reactivity modes of lithium(aryl)(boryl)amide, 4 , when it is reacted with chlorosilanes such as SiCl 4 and MeSiHCl 2 , and chlorophosphine, Ph 2 PCl. Thus, the reaction of lithium(aryl)(boryl)amide, 4 , with MeSiHCl 2 leads exclusively to an N -substitution product, 6 . On the other hand, the reaction of 4 with SiCl 4 and Ph 2 PCl proceeds completely differently affording exclusively p -aryl- C -substitution products, 5 and 7 , respectively. Nucleophilic substitution reaction of (boryl)(aryl)lithium-amide leads to two different types of products: N - vs. p -aryl- C -substitution based on electrophile.