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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

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Publication details

The article was received on 05 Aug 2018, accepted on 10 Sep 2018 and first published on 10 Sep 2018


Article type: Communication
DOI: 10.1039/C8DT03201G
Citation: Dalton Trans., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C8DT03201G

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