2020
DOI: 10.1039/d0cc06584f
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Deep eutectic solvent-catalyzed Meyer–Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions

Abstract: Faster, milder, greener…better! The Meyer–Schuster rearrangement is disclosed for the first time in a deep eutectic solvent, namely FeCl3·6H2O/glycerol (3 : 1), enabling the reaction at room temperature, under air and with short reaction times.

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Cited by 20 publications
(13 citation statements)
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“…21 Furthermore, the exploitation of DESs as solvents and/or catalysts for organic reactions has been a recent and intense area of study. Several archetypical reactions [22][23][24][25] including Grignard and organolithium additions [26][27][28] as well as the preparation of pharmaceutical active ingredients, 29 have been optimised in these protic media.…”
mentioning
confidence: 99%
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“…21 Furthermore, the exploitation of DESs as solvents and/or catalysts for organic reactions has been a recent and intense area of study. Several archetypical reactions [22][23][24][25] including Grignard and organolithium additions [26][27][28] as well as the preparation of pharmaceutical active ingredients, 29 have been optimised in these protic media.…”
mentioning
confidence: 99%
“…Olefin-based radical syntheses in DESs in the presence of air have recently been reported in the form of Cu-catalysed polymerisation 36 and Meyer–Schuster rearrangement. 29 Having recently reported atmospheric oxygen mediated TEC and ATE reactions, 37 we next investigated these conditions and their scope within the context of the DES solvent system (Scheme 1). Due to lack of requirement for an initiator or sensitiser, these initiation conditions further strengthen the ‘green’ chemistry characteristics of this methodology, with high atom economy and use of non-volatile, recyclable solvents.…”
mentioning
confidence: 99%
“…Similarly, the iron-based eutectic mixture FeCl 3 .6H 2 O:glycerol (3:1) was described as a solvent and Lewis acid catalyst for performing the Meyer–Schuster rearrangement of propargylic alcohols to afford the corresponding ketones or aldehydes in excellent yields. Moreover, the catalytic DESs were recycled up to 10 times without losing their activity ( Figure 39 , Table 6 , entry 5) [ 115 ].…”
Section: Miscellaneousmentioning
confidence: 99%
“…A bright example of a green transition-metal-catalyzed transformations has recently been reported by González-Sabín’s and García-Álvarez’s groups on the Meyer-Schuster rearrangement of propargylic alcohols [ 169 ]. In this work, the cheap eutectic mixture FeCl 3 ·6H 2 O/Gly (3:1) successfully mediated the reaction of non-functionalized terminal and internal alkynols to their corresponding α , β -unsaturated carbonyl compounds with full conversions and yields up to 92%.…”
Section: Recent Advances In the Employment Of Dess Both As Non-innocent Solvents And As Active Co-catalystsmentioning
confidence: 99%