Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions
Vladimir Viktorovich Voronin
1
,
Vladimir V Voronin
2, 3, 4, 5
,
Maria S Ledovskaya
1, 2, 3, 4, 5
,
Konstantin S Rodygin
1, 6
,
Valentine P. Ananikov
1, 2, 3, 4, 5, 6, 7
2
Institute of Chemistry
4
Peterhof
5
Russia
|
Publication type: Journal Article
Publication date: 2020-04-08
scimago Q1
wos Q1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Organic Chemistry
Abstract
A method for protection of alcohols with vinyl groups is suggested and studied in detail. The procedures of protection and deprotection via vinylation and devinylation reactions are evaluated. Vinylation reaction is performed using cheap and convenient calcium carbide reagent. Stability of the vinyl group under various conditions is examined. The vinyl group is found to be stable under basic conditions and labile under acidic conditions. The vinyl protecting group shows high tolerance to functional groups and good compatibility with common synthetic reagents. Applicability of the procedure in the Suzuki and Sonogashira catalytic reactions and its flexible utilization in the reaction with Grignard reagent are demonstrated.
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Metrics
35
Total citations:
35
Citations from 2025:
5
(14.71%)
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GOST
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Voronin V. V. et al. Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions // Organic Chemistry Frontiers. 2020. Vol. 7. No. 11. pp. 1334-1342.
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Voronin V. V., Voronin V. V., Ledovskaya M. S., Rodygin K. S., Ananikov V. P. Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions // Organic Chemistry Frontiers. 2020. Vol. 7. No. 11. pp. 1334-1342.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/D0QO00202J
UR - https://xlink.rsc.org/?DOI=D0QO00202J
TI - Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions
T2 - Organic Chemistry Frontiers
AU - Voronin, Vladimir Viktorovich
AU - Voronin, Vladimir V
AU - Ledovskaya, Maria S
AU - Rodygin, Konstantin S
AU - Ananikov, Valentine P.
PY - 2020
DA - 2020/04/08
PB - Royal Society of Chemistry (RSC)
SP - 1334-1342
IS - 11
VL - 7
SN - 2052-4110
SN - 2052-4129
ER -
Cite this
BibTex (up to 50 authors)
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@article{2020_Voronin,
author = {Vladimir Viktorovich Voronin and Vladimir V Voronin and Maria S Ledovskaya and Konstantin S Rodygin and Valentine P. Ananikov},
title = {Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions},
journal = {Organic Chemistry Frontiers},
year = {2020},
volume = {7},
publisher = {Royal Society of Chemistry (RSC)},
month = {apr},
url = {https://xlink.rsc.org/?DOI=D0QO00202J},
number = {11},
pages = {1334--1342},
doi = {10.1039/D0QO00202J}
}
Cite this
MLA
Copy
Voronin, Vladimir V., et al. “Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions.” Organic Chemistry Frontiers, vol. 7, no. 11, Apr. 2020, pp. 1334-1342. https://xlink.rsc.org/?DOI=D0QO00202J.
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