Chan‐Lam‐type Azidation and One‐Pot CuAAC under Cu^I‐Zeolite Catalysis

Abstract

The copper(I)‐exchanged zeolite CuI‐USY proved to efficiently catalyze the direct azidation of arylboronic acids with sodium azide under simple and practical conditions, namely at room temperature under air with methanol as solvent and without any additive. This easy‐to‐prepare and cheap catalytic material has been demonstrated to be recyclable and the mild azidation conditions further showed good functional‐group tolerance, leading to a variety of substituted (hetero)aryl azides (18 examples). Interestingly, the azidation reaction has been successfully coupled to a CuAAC reaction, thus allowing access to triazoles from arylboronic acids via a one‐pot CuI‐catalyzed process.

Dinuclear Copper Complex Immobilized on a Janus-Type Material as an Interfacial Heterogeneous Catalyst for Green Synthesis

“…To further explore the applicability of catalyst 6 in organic transformations, it was employed for the synthesis of 1,4-diphenyl-1,2,3-triazole ( 7 ) with phenylboronic acid as the coupling reagent . Product 7 was obtained in 72% yield (Scheme a) in aqueous solution with only 1% of the catalyst at 70 °C after 7 h. Furthermore, catalyst 6 was employed for the synthesis of some biologically active compounds.…”

Synthesis and Antitumor Activity of 1-Substituted 1,2,3-Triazole-Mollugin Derivatives

“…The 1-substituted 1,2,3-triazole-mollugin derivatives were synthesized using a copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of the corresponding O -propargylated mollugin ( 3 ) with different substituted aromatic azides ( Scheme 2 ) [ 18 , 19 ]. In addition, all aromatic azides were prepared from corresponding boronic acid with sodium azide in the presence of CuSO 4 in methanol (MeOH) without further purification [ 27 , 28 ].…”

“…All compounds were named using the ACD40 Name-Pro program, which is based on IUPAC rules. Azides ( 4 ) were synthesized according to procedures previously described in the literature [ 27 , 28 ].…”

Base‐Free Copper‐Catalyzed Azide‐Alkyne Click Cycloadditions (CuAAc) in Natural Deep Eutectic Solvents as Green and Catalytic Reaction Media**

“…1‐(4‐methoxyphenyl)‐4‐phenyl‐1H‐1,2,3‐triazole ( 3 r ) [56] . Yellow solid; mp 164–165 °C; 1 H NMR (500 MHz, CDCl 3 ) δ =8.20 (br.…”