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Issue 41, 2018

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

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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

Supplementary files

Article information


Submitted
05 Aug 2018
Accepted
10 Sep 2018
First published
10 Sep 2018

Dalton Trans., 2018,47, 14411-14415
Article type
Communication

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

D. Dhara, T. Vijayakanth, M. K. Nayak, P. Kalita, R. Boomishankar, C. B. Yildiz, V. Chandrasekhar and A. Jana, Dalton Trans., 2018, 47, 14411 DOI: 10.1039/C8DT03201G

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