Solvent-free synthesis of quaternary alpha-hydroxy alpha-trifluoromethyl diazenes: the key step of a nucleophilic formylation strategy
Description
An 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.
Abstract
Ministerio de Economía y Competitividad de España. CTQ2013-48164-C2-1-P y CTQ2013-48164-C2-2-P
Abstract
Fondos FEDER y Junta de Andalucía. 2012/FQM 1078
Additional details
- URL
- https://idus.us.es/handle//11441/134024
- URN
- urn:oai:idus.us.es:11441/134024
- Origin repository
- USE