Organic Letters p. 2750 - 2753 (2016)
Update date:2022-08-04
Topics: Regioselectivity Yield Reduction Catalytic hydrogenation Nucleophilic addition Chemoselective TLC (thin-layer chromatography) NMR (nuclear magnetic resonance) Isocyanates Purification Workup Formamides Hydride Transfer Functional Group Tolerance Stoichiometric Byproduct Zirconocene Inert atmosphere Solvent system
Pace, Vittorio
De La Vega-Hernández, Karen
Urban, Ernst
Langer, Thierry
Addition of the in situ generated Schwartz reagent to widely available isocyanates constitutes a chemoselective, high-yielding, and versatile approach to the synthesis of variously functionalized formamides. Steric and electronic factors or the presence of sensitive functionalities (esters, nitro groups, nitriles, alkenes) do not compromise the potential of the method. Full preservation of the stereochemical information contained in the starting materials is observed. The use of formamides in the nucleophilic addition of organometallic reagents (Chida-Sato allylation, Charette-Huang addition to imidoyl triflate activated amides, Matteson homologation of boronic esters) is briefly investigated.
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