Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 33, Pages 7848-7854Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob00766j
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Funding
- University of Vienna
- OEAD
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The addition of carbon (Grignard and organolithium reagents) and hydride nucleophiles (Schwartz reagent) to isocyanates and isothiocyanates constitutes a versatile, direct and high yielding approach to the synthesis of functionalized (thio)amide derivatives including haloamides and formamides. The chemo-selective delivery of a nucleophilic (eventually configurationally stable) organometallic species to a given iso(thio)cyanate is the crucial parameter for the success of the strategy. Thus, the influence of the factors governing classical methodologies (e.g. dehydrative condensation) such as steric hindrance and electronic properties of the reactants become practically negligible.
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