Mendeleev Communications
,  том 33 ,  издание 4 ,  страницы 458-460

A facile synthesis of 2-ethynylpyrroles by ButOK-assisted room temperature deprotection of 2-(acylethynyl)pyrroles

Тип публикации: Journal Article
Дата публикации: 2023-07-17
scimago Q3
wos Q3
БС1
SJR: 0.305
CiteScore: 3.0
Impact factor: 1.7
ISSN: 09599436, 1364551X
General Chemistry
Краткое описание
Available N-substituted 2-(acylethynyl)pyrroles undergo room temperature deprotection in the ButOK/THF system to give 2-ethynylpyrroles in 82–92% yields. Quantum-chemical calculations (B2PLYP/6-311G**//B3LYP/6-311G**+C-PCM/THF) show that the cleavage of ethynyl–acyl bond via the proton transfer from ButOK with formation of potassium acylate and 2-methylpropene is thermo-dynamically much more preferred compared to alternative nucleophilic attack of tert-butoxide anion at the acyl carbon (ΔG = –35.1 vs. –2.7 kcal mol-1).
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Tomilin D. N. et al. A facile synthesis of 2-ethynylpyrroles by ButOK-assisted room temperature deprotection of 2-(acylethynyl)pyrroles // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 458-460.
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Tomilin D. N., Sobenina L. N., Trofimov A. B., Belogolova A. M., Ushakov I. A., Shaglaeva N. S., Trofimov B. A. A facile synthesis of 2-ethynylpyrroles by ButOK-assisted room temperature deprotection of 2-(acylethynyl)pyrroles // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 458-460.
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TY - JOUR
DO - 10.1016/j.mencom.2023.06.005
UR - https://doi.org/10.1016/j.mencom.2023.06.005
TI - A facile synthesis of 2-ethynylpyrroles by ButOK-assisted room temperature deprotection of 2-(acylethynyl)pyrroles
T2 - Mendeleev Communications
AU - Tomilin, D. N.
AU - Sobenina, Lyubov Nikolaevna
AU - Trofimov, A B
AU - Belogolova, Alexandra M.
AU - Ushakov, I A
AU - Shaglaeva, N. S.
AU - Trofimov, B. A.
PY - 2023
DA - 2023/07/17
PB - OOO Zhurnal "Mendeleevskie Soobshcheniya"
SP - 458-460
IS - 4
VL - 33
SN - 0959-9436
SN - 1364-551X
ER -
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@article{2023_Tomilin,
author = {D. N. Tomilin and Lyubov Nikolaevna Sobenina and A B Trofimov and Alexandra M. Belogolova and I A Ushakov and N. S. Shaglaeva and B. A. Trofimov},
title = {A facile synthesis of 2-ethynylpyrroles by ButOK-assisted room temperature deprotection of 2-(acylethynyl)pyrroles},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {OOO Zhurnal "Mendeleevskie Soobshcheniya"},
month = {jul},
url = {https://doi.org/10.1016/j.mencom.2023.06.005},
number = {4},
pages = {458--460},
doi = {10.1016/j.mencom.2023.06.005}
}
MLA
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Tomilin, D. N., et al. “A facile synthesis of 2-ethynylpyrroles by ButOK-assisted room temperature deprotection of 2-(acylethynyl)pyrroles.” Mendeleev Communications, vol. 33, no. 4, Jul. 2023, pp. 458-460. https://doi.org/10.1016/j.mencom.2023.06.005.