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Article

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)
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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MDPI and ACS Style

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. https://0-doi-org.brum.beds.ac.uk/10.3390/inorganics6030069

AMA Style

Raut RK, Amin SF, Sahoo P, Kumar V, Majumdar M. One-Pot Synthesis of Heavier Group 14 N-Heterocyclic Carbene Using Organosilicon Reductant. Inorganics. 2018; 6(3):69. https://0-doi-org.brum.beds.ac.uk/10.3390/inorganics6030069

Chicago/Turabian Style

Raut, Ravindra K., Sheikh F. Amin, Padmini Sahoo, Vikas Kumar, and Moumita Majumdar. 2018. "One-Pot Synthesis of Heavier Group 14 N-Heterocyclic Carbene Using Organosilicon Reductant" Inorganics 6, no. 3: 69. https://0-doi-org.brum.beds.ac.uk/10.3390/inorganics6030069

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