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Inorganics 2018, 6(3), 69; https://doi.org/10.3390/inorganics6030069

One-Pot Synthesis of Heavier Group 14 N-Heterocyclic Carbene Using Organosilicon Reductant

Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan, Pune-411008, India
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Received: 6 June 2018 / Revised: 25 June 2018 / Accepted: 30 June 2018 / Published: 12 July 2018
(This article belongs to the Special Issue Coordination Chemistry of Silicon)
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Abstract

Syntheses of heavier Group 14 analogues of “Arduengo-type” N-heterocyclic carbene majorly involved the use of conventional alkali metal-based reducing agents under harsh reaction conditions. The accompanied reductant-derived metal salts and chances of over-reduced impurities often led to isolation difficulties in this multi-step process. In order to overcome these shortcomings, we have used 1,4-bis-(trimethylsilyl)-1,4-diaza-2,5-cyclohexadiene as a milder reducing agent for the preparation of N-heterocyclic germylenes (NHGe) and stannylenes (NHSn). The reaction occurs in a single step with moderate yields from the mixture of N-substituted 1,4-diaza-1,3-butadiene, E(II) (E(II) = GeCl2·dioxane, SnCl2) and the organosilicon reductant. The volatile byproducts trimethylsilyl chloride and pyrazine could be removed readily under vacuum. No significant over reduction was observed in this process. However, N-heterocyclic silylene (NHSi) could not be synthesized using an even stronger organosilicon reductant under thermal and photochemical conditions. View Full-Text
Keywords: organosilicon; reductant; N-Heterocyclic tetrylene; salt-free organosilicon; reductant; N-Heterocyclic tetrylene; salt-free
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Raut, R.K.; Amin, S.F.; Sahoo, P.; Kumar, V.; Majumdar, M. One-Pot Synthesis of Heavier Group 14 N-Heterocyclic Carbene Using Organosilicon Reductant. Inorganics 2018, 6, 69.

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