Nitroalkanes have proven to be a valuable and versatile class of compounds in organic synthesis. Transformations that permit the interconversion of nitro groups into other functionalities are therefore of primary importance as they potentially broaden the utility of nitroalkanes as intermediates in synthesis. Our group has recently reported an unprecedented metal-free protocol for the reduction of nitro derivatives into amines based on the use of trichlorosilane (HSiCl3) , an inexpensive and readily commercially available compound produced as a waste by the silicon industry. Specifically, it was observed that nitro compounds could be reduced to the corresponding amines when reacted in the presence of HSiCl3 and a tertiary amine under mild reaction conditions. However, in case of aliphatic substrates, depending on their nature, the corresponding cyano derivative could be observed as a substantial reaction byproduct. Herein we report our efforts for the optimization of this protocol that resulted in the chemoselective, divergent transformation of aliphatic nitro compounds into the corresponding amine or cyano derivative by fine tuning of the reaction conditions (unpublished results). The reduction protocol relies on the use of inexpensive and readily available chemicals, features a simple experimental procedure, and is performed under mild conditions. Additionally, the use of transition metals typically used for the reduction of nitro compounds is avoided, providing an environmentally friendly reaction that excludes the contamination of the products by potentially toxic metal impurities.

Trichlorosilane : a versatile reagent for nitroalkanes transformations / M. Pirola, M. Orlandi, M. Benaglia. ((Intervento presentato al convegno Merk and Elsevier Young Chemists Symposium tenutosi a Rimini nel 2018.

Trichlorosilane : a versatile reagent for nitroalkanes transformations

M. Pirola
Co-primo
;
M. Orlandi
Co-primo
;
M. Benaglia
Ultimo
2018-11-21

Abstract

Nitroalkanes have proven to be a valuable and versatile class of compounds in organic synthesis. Transformations that permit the interconversion of nitro groups into other functionalities are therefore of primary importance as they potentially broaden the utility of nitroalkanes as intermediates in synthesis. Our group has recently reported an unprecedented metal-free protocol for the reduction of nitro derivatives into amines based on the use of trichlorosilane (HSiCl3) , an inexpensive and readily commercially available compound produced as a waste by the silicon industry. Specifically, it was observed that nitro compounds could be reduced to the corresponding amines when reacted in the presence of HSiCl3 and a tertiary amine under mild reaction conditions. However, in case of aliphatic substrates, depending on their nature, the corresponding cyano derivative could be observed as a substantial reaction byproduct. Herein we report our efforts for the optimization of this protocol that resulted in the chemoselective, divergent transformation of aliphatic nitro compounds into the corresponding amine or cyano derivative by fine tuning of the reaction conditions (unpublished results). The reduction protocol relies on the use of inexpensive and readily available chemicals, features a simple experimental procedure, and is performed under mild conditions. Additionally, the use of transition metals typically used for the reduction of nitro compounds is avoided, providing an environmentally friendly reaction that excludes the contamination of the products by potentially toxic metal impurities.
Settore CHIM/06 - Chimica Organica
Trichlorosilane : a versatile reagent for nitroalkanes transformations / M. Pirola, M. Orlandi, M. Benaglia. ((Intervento presentato al convegno Merk and Elsevier Young Chemists Symposium tenutosi a Rimini nel 2018.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/619913
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