Amberlite IRA900N₃as a New Catalyst for the Azidation of α,β-Unsaturated Ketones under Solvent-Free Conditions

Abstract

Amberlite IRA900N3 is an excellent organocatalyst for the azidation of alpha,beta-unsaturated ketones with trimethylsilyl azide under solvent-free conditions. By avoiding the use of metallic species and of the organic reaction medium, the procedure is a green tool for the preparation of beta-azido ketones under mild conditions with yields from good to excellent. The catalyst can be recovered and re-used with no loss of its efficiency.

Preparation and Use of Polystyryl‐DABCOF2: An Efficient Recoverable and Reusable Catalyst for β‐Azidation of α,β‐Unsaturated Ketones in Water

“…Therefore, in agreement to our previously reported results,8c it can be concluded that the reaction proceeds according to the plausible mechanism depicted in Scheme .…”

“…According to our previous results,8a–c the recovered catalysts resulted from the complete substitution of both fluoride ions by azido ions with formation of volatile trimethylsilyl fluoride, b.p. 16 °C.…”

“…We have been interested in the use of organic ammonium fluorides for activating SiN and SiO8 bonds and within this research we have reported an alternative protocol for the β‐azidation of α,β‐unsaturated ketones based on the use of recoverable Amberlite IRA900F as catalyst under solvent‐free conditions (SolFC) 8c…”

“…22), we also noticed that in this process the reaction mixture showed an evident tendency to stick with the polymer resin. Therefore compared to other processes studied by our group, larger amounts of organic solvent were needed to isolate the products 8c…”

Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis

“…The catalyst was recycled and reused in four more runs without loss of its efficiency and activity. 15 (B) Regio-and stereoselective bromoazidation of alkenes was carried out using N-bromosuccinimide (NBS) and TMSN 3 as bromine and azide source with good yields. Zinc triflate [Zn(OTf) 2 ] was an efficient catalyst for the synthesis of anti-1,2-bromoazide with high selectivity.…”