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

Vladimir V. Voronin, Maria S. Ledovskaya, Konstantin S. Rodygin, Valentine P. Ananikov

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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.

Original languageEnglish
Pages (from-to)1334-1342
Number of pages9
JournalOrganic Chemistry Frontiers
Volume7
Issue number11
Early online date8 Apr 2020
DOIs
StatePublished - 7 Jun 2020

Scopus subject areas

  • Organic Chemistry

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