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

Debabrata Dhara; Thangavel Vijayakanth; Mithilesh Kumar Nayak; Pankaj Kalita; Ramamoorthy Boomishankar; Cem Burak Yildiz; Vadapalli Chandrasekhar; Anukul Jana

doi:10.1039/C8DT03201G

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

Debabrata Dhara,

^a Thangavel Vijayakanth,

^b Mithilesh Kumar Nayak,^a Pankaj Kalita,^c Ramamoorthy Boomishankar,

*^b Cem Burak Yildiz,

*^d Vadapalli Chandrasekhar

*^ae and Anukul Jana

*^a

Author affiliations

* Corresponding authors

^a Tata Institute of Fundamental Research Centre for Interdisciplinary Sciences 21, Brundavan Colony, Narsingi, Hyderabad-500075, India
E-mail: ajana@tifrh.res.in

^b Department of Chemistry, Indian Institute of Science Education and Research (IISER), Pune, Dr Homi Bhabha Road, Pune 411008, India
E-mail: boomi@iiserpune.ac.in

^c National Institute of Science Education and Research, HBNI, Bhimpur-Padanpur, Jatni, Khurda, Bhubaneswar-752050, Odisha, India

^d Department of Medicinal and Aromatic Plants, University of Aksaray, Aksaray, Turkey
E-mail: cemburakyildiz@aksaray.edu.tr

^e Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India
E-mail: vc@iitk.ac.in

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.

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DOI: https://doi.org/10.1039/C8DT03201G
Article type: Communication
Submitted: 05 Aug 2018
Accepted: 10 Sep 2018
First published: 10 Sep 2018

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Dalton Trans., 2018,47, 14411-14415

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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, 47, 14411 DOI: 10.1039/C8DT03201G

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Dalton Transactions

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

Abstract

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

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