Article
Solvent-free synthesis of quaternary alpha-hydroxy alpha-trifluoromethyl diazenes: the key step of a nucleophilic formylation strategy
Author/s | Matador Martínez, Esteban
![]() ![]() ![]() ![]() ![]() ![]() Monge Fernández, David ![]() ![]() ![]() ![]() ![]() ![]() ![]() Fernández Fernández, Rosario Fátima ![]() ![]() ![]() ![]() ![]() ![]() ![]() Lassaletta Simón, José María |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2016 |
Deposit Date | 2022-06-03 |
Published in |
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Abstract | 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 ... 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. |
Funding agencies | Ministerio de Economía y Competitividad (MINECO). España European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER) Junta de Andalucía Universidad de Sevilla |
Project ID. | CTQ2013-48164-C2-1-P
![]() CTQ2013-48164-C2-2-P ![]() 2012/FQM 1078 ![]() |
Citation | Matador Martínez, E., Monge Fernández, D., Fernández Fernández, R.F. y Lassaletta Simón, J.M. (2016). Solvent-free synthesis of quaternary alpha-hydroxy alpha-trifluoromethyl diazenes: the key step of a nucleophilic formylation strategy. Green Chemistry, 18 (14), 4042-4050. |
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