Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles: N- vs. p-aryl-C-nucleophilic substitution??

Dalton Transactions Pub Date: 2018-09-10 DOI: 10.1039/C8DT03201G

Abstract

Herein we report two different reactivity modes of lithium(aryl)(boryl)amide, 4, when it is reacted with chlorosilanes such as SiCl4 and MeSiHCl2, and chlorophosphine, Ph2PCl. Thus, the reaction of lithium(aryl)(boryl)amide, 4, with MeSiHCl2 leads exclusively to an N-substitution product, 6. On the other hand, the reaction of 4 with SiCl4 and Ph2PCl proceeds completely differently affording exclusively p-aryl-C-substitution products, 5 and 7, respectively.

Graphical abstract: Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles: N- vs. p-aryl-C-nucleophilic substitution
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