Meyer–Schuster rearrangement of propargylic alcohols mediated by phosphorus-containing Brønsted acid catalysts

Radtanajiravong, Lalita; Peters, Jake; Hummell, Jake; Díez‐González, Silvia

doi:10.1039/d2ob01259f

Cited by 3 publications

(1 citation statement)

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“…This phosphorus-based family was further applied to Brønsted-acid catalysed Meyer-Schuster rearrangement of propargylic alcohols. 26 Accordingly, we envisaged that this biogenic phosphorus-containing acid could be a good candidate in the direct nucleophilic substitutions of allylic alcohols to provide a sustainable approach and effectively broaden the scope of aniline nucleophiles. Herein, we report the first use of phytic acid as a Brønsted acid catalyst for the amination of allylic alcohols (Scheme 1d).…”

Section: Introductionmentioning

confidence: 99%

Naturally occurring phytic acid: an advanced Brønsted acid catalyst for direct amination reactions of allylic alcohols

Pham,

Chavasiri,

Radtanajiravong

2024

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

Naturally occurring phytic acid: an advanced Brønsted acid catalyst for direct amination reactions of allylic alcohols

Pham,

Chavasiri,

Radtanajiravong

2024

Org. Biomol. Chem.

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The Meyer–Schuster Rearrangement

Vidari,

Chiodi,

Porta

et al. 2024

Organic Reactions

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The Meyer–Schuster rearrangement corresponds to a formal 1,3‐shift of a propargylic alcohol to afford the corresponding α,β‐unsaturated carbonyl compound via tautomerization of an allenol intermediate. The original acidic and harsh conditions have been replaced with mild and selective conditions that are compatible with a variety of functional and protecting groups. Commonly employed strategies include the activation of propargylic alcohols as esters, transition‐metal catalysis (e.g., gold complexes and oxometal complexes), and the C–H bond activation of terminal propargylic alcohols by transition‐metal insertion. The Meyer–Schuster rearrangement has been extended to all classes of propargylic alcohols and esters, including C sp ‐heteroatom‐substituted alkynols, as well as to propargylic amine derivatives (i.e., the aza‐Meyer–Schuster rearrangement). Moreover, the rearrangement can be employed in inter‐ and intramolecular one‐pot consecutive reactions, wherein multiple carbon–carbon and/or carbon–heteroatom bonds are formed. The Meyer–Schuster reaction exhibits a high atom economy, simple experimental procedures, and good‐to‐excellent product yields and stereoselectivities. Moreover, starting materials are easily accessible, and any toxic metals are employed in substoichiometric amounts. As such, the Meyer–Schuster rearrangement compares favorably with other standard protocols, such as the Wittig reaction, for the preparation of α,β‐unsaturated carbonyl compounds and derivatives. This review covers the literature since the identification of the reaction up to the end of 2020 and includes relevant references through November 2023. Both the mechanistic features and the regio‐ and stereoselectivity issues are discussed as they relate to the reaction conditions. The scope and limitations of the reaction are presented, as are a selection of synthetic applications, several general experimental procedures, and a comparison of the Meyer–Schuster rearrangement with other known methods. Finally, the tabular survey highlights the broad range of starting materials and products possible with the Meyer–Schuster rearrangement.

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Transition metal-catalyzed redox-neutral 1,3-dienylation of propargylic esters and divergent synthesis

Tang,

Dai,

Zhou

et al. 2024

Org. Chem. Front.

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Meyer–Schuster rearrangement of propargylic alcohols mediated by phosphorus-containing Brønsted acid catalysts

Abstract: Commercially available (aqueous) hypophosphorus acid is an efficient catalyst for the synthesis of α,β-unsaturated carbonyl compounds from their corresponding propargylic alcohols. Reactions were carried out in technical toluene in the...

Cited by 3 publications

References 20 publications

Naturally occurring phytic acid: an advanced Brønsted acid catalyst for direct amination reactions of allylic alcohols

Naturally occurring phytic acid: an advanced Brønsted acid catalyst for direct amination reactions of allylic alcohols

The Meyer–Schuster Rearrangement

Transition metal-catalyzed redox-neutral 1,3-dienylation of propargylic esters and divergent synthesis

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