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Solvent-free synthesis of quaternary α-hydroxy α-trifluoromethyl diazenes: the key step of a nucleophilic formylation strategy

AuthorsMatador, Esteban; Monge, David; Fernández, Rosario; Lassaletta, José M.
Issue Date2016
PublisherRoyal Society of Chemistry
CitationGreen Chemistry 18(14): 4042-4050 (2016)
AbstractAn efficient, scalable and operationally simple one-pot, 2-step strategy for the nucleophilic formylation of trifluoromethyl ketones is presented. The key step is an unprecedented diaza-carbonyl-ene reaction of formaldehyde tert-butyl hydrazone and trifluoromethyl ketones under solvent-free conditions. This reaction proved to be very fast, clean and high-yielding, affording densely functionalised α-hydroxy α-trifluoromethyl diazenes. The ensuing diazene-to-aldehyde transformation, avoiding protection/deprotection reactions and chromatographic purifications, and subsequent derivatizations in a one-pot fashion provide a direct entry to a variety of useful trifluoromethylated building blocks.
Publisher version (URL)http://dx.doi.org/10.1039/C6GC00408C
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