Abstract: Since the introduction of 2-methyltetrahydrofuran as an useful alternative to the classical tetrahydrofuran, there has been a continuous interest in the synthetic community operating at academic and industrial towards it. In particular, the much higher stability that basic organometallic reagents display in 2-methyltetrahydrofuran makes it suitable for processes involving such sensitive species including asymmetric transformations. The easy formation of an azeotropic mixture with water, the substantial immiscibility with water, and the fact it derives from natural sources (corncobs or bagasse), allow to consider it in agreement with the Anastas’ Geen Chemistry principles. In this minireview, selected examples of its employment in organometallic transformations ranging from carbanions to radical and transition metal-catalyzed processes are provided. Graphical abstract: [Figure not available: see fulltext.]

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry / S. Monticelli, L. Castoldi, I. Murgia, R. Senatore, E. Mazzeo, J. Wackerlig, E. Urban, T. Langer, V. Pace. - In: MONATSHEFTE FÜR CHEMIE. - ISSN 0026-9247. - 148:1(2016 Dec 07), pp. 37-48. [10.1007/s00706-016-1879-3]

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

L. Castoldi
Secondo
;
2016

Abstract

Abstract: Since the introduction of 2-methyltetrahydrofuran as an useful alternative to the classical tetrahydrofuran, there has been a continuous interest in the synthetic community operating at academic and industrial towards it. In particular, the much higher stability that basic organometallic reagents display in 2-methyltetrahydrofuran makes it suitable for processes involving such sensitive species including asymmetric transformations. The easy formation of an azeotropic mixture with water, the substantial immiscibility with water, and the fact it derives from natural sources (corncobs or bagasse), allow to consider it in agreement with the Anastas’ Geen Chemistry principles. In this minireview, selected examples of its employment in organometallic transformations ranging from carbanions to radical and transition metal-catalyzed processes are provided. Graphical abstract: [Figure not available: see fulltext.]
Carbanions; Green chemistry; Grignard reaction; Solvent effect
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/890708
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