Synthesis of phenol derivatives from cyclopentenones with arynes as key intermediates

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Standard

Synthesis of phenol derivatives from cyclopentenones with arynes as key intermediates. / Telese, Dario; Staudt, Markus; Bunch, Lennart.

In: Results in Chemistry, Vol. 4, 100412, 2022.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Telese, D, Staudt, M & Bunch, L 2022, 'Synthesis of phenol derivatives from cyclopentenones with arynes as key intermediates', Results in Chemistry, vol. 4, 100412. https://doi.org/10.1016/j.rechem.2022.100412

APA

Telese, D., Staudt, M., & Bunch, L. (2022). Synthesis of phenol derivatives from cyclopentenones with arynes as key intermediates. Results in Chemistry, 4, [100412]. https://doi.org/10.1016/j.rechem.2022.100412

Vancouver

Telese D, Staudt M, Bunch L. Synthesis of phenol derivatives from cyclopentenones with arynes as key intermediates. Results in Chemistry. 2022;4. 100412. https://doi.org/10.1016/j.rechem.2022.100412

Author

Telese, Dario ; Staudt, Markus ; Bunch, Lennart. / Synthesis of phenol derivatives from cyclopentenones with arynes as key intermediates. In: Results in Chemistry. 2022 ; Vol. 4.

Bibtex

@article{0e22eb8923d54860a9505af008d306e5,
title = "Synthesis of phenol derivatives from cyclopentenones with arynes as key intermediates",
abstract = "Phenols are frequent motifs in drug discovery and material sciences, thus their synthesis continue to attract attention. Herein we present a five-step cascade reaction for the synthesis of phenol derivatives from their corresponding 2-trimethylsilylcyclopentenone and arynophile precursors, and iodoform. The methodology builds on previously reported anion-accelerated electrocyclic ring-opening which provides the corresponding 3-iodo-2-trimethylsilylphenoxy anion. A Brook-like rearrangement provides the key benzyne intermediate, which reacts in situ with the arynophile. The reactivity of different classes of arynophiles were investigated, and it was shown that under the optimized conditions [4 + 2] and [2 + 2] cycloadditions as well as nucleophilic addition were productive, while [3 + 2] was not. Isolated yields were up to 40%.",
keywords = "Aryne, Brook-like rearrangement, Electrocyclic Ring-opening, Phenols",
author = "Dario Telese and Markus Staudt and Lennart Bunch",
note = "Publisher Copyright: {\textcopyright} 2022 The Author(s)",
year = "2022",
doi = "10.1016/j.rechem.2022.100412",
language = "English",
volume = "4",
journal = "Results in Chemistry",
issn = "2211-7156",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis of phenol derivatives from cyclopentenones with arynes as key intermediates

AU - Telese, Dario

AU - Staudt, Markus

AU - Bunch, Lennart

N1 - Publisher Copyright: © 2022 The Author(s)

PY - 2022

Y1 - 2022

N2 - Phenols are frequent motifs in drug discovery and material sciences, thus their synthesis continue to attract attention. Herein we present a five-step cascade reaction for the synthesis of phenol derivatives from their corresponding 2-trimethylsilylcyclopentenone and arynophile precursors, and iodoform. The methodology builds on previously reported anion-accelerated electrocyclic ring-opening which provides the corresponding 3-iodo-2-trimethylsilylphenoxy anion. A Brook-like rearrangement provides the key benzyne intermediate, which reacts in situ with the arynophile. The reactivity of different classes of arynophiles were investigated, and it was shown that under the optimized conditions [4 + 2] and [2 + 2] cycloadditions as well as nucleophilic addition were productive, while [3 + 2] was not. Isolated yields were up to 40%.

AB - Phenols are frequent motifs in drug discovery and material sciences, thus their synthesis continue to attract attention. Herein we present a five-step cascade reaction for the synthesis of phenol derivatives from their corresponding 2-trimethylsilylcyclopentenone and arynophile precursors, and iodoform. The methodology builds on previously reported anion-accelerated electrocyclic ring-opening which provides the corresponding 3-iodo-2-trimethylsilylphenoxy anion. A Brook-like rearrangement provides the key benzyne intermediate, which reacts in situ with the arynophile. The reactivity of different classes of arynophiles were investigated, and it was shown that under the optimized conditions [4 + 2] and [2 + 2] cycloadditions as well as nucleophilic addition were productive, while [3 + 2] was not. Isolated yields were up to 40%.

KW - Aryne

KW - Brook-like rearrangement

KW - Electrocyclic Ring-opening

KW - Phenols

U2 - 10.1016/j.rechem.2022.100412

DO - 10.1016/j.rechem.2022.100412

M3 - Journal article

AN - SCOPUS:85133486711

VL - 4

JO - Results in Chemistry

JF - Results in Chemistry

SN - 2211-7156

M1 - 100412

ER -

ID: 315250203