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Issue 11, 2020
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Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions

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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.

Graphical abstract: Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions

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Supplementary files

Article information


Submitted
12 Feb 2020
Accepted
04 Apr 2020
First published
08 Apr 2020

Org. Chem. Front., 2020,7, 1334-1342
Article type
Research Article

Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions

V. V. Voronin, M. S. Ledovskaya, K. S. Rodygin and V. P. Ananikov, Org. Chem. Front., 2020, 7, 1334
DOI: 10.1039/D0QO00202J

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