1D Azido bridged Cu(II) coordination polymer with 1,3‐oxazolidine ligand as an effective catalyst for green click synthesis of 1,2,3‐triazoles

Abstract

A new 1D azido bridged Cu(II) coordination polymer with 1,3‐oxazolidine based ligand, [Cu(H3L)(μ1,3‐N3)(N3)]n (1), was synthesized and characterized by elemental analysis and spectroscopic methods. The structure of 1 was also determined by single crystal X‐ray analysis which indicated the 1D polymeric chain is generated by end‐to‐end (EE) azide bridge. The obtained compound was employed as catalyst in green click synthesis of β‐hydroxy‐1,2,3‐triazoles from one‐pot three‐component cycloaddition reaction of epoxide‐azide‐alkyne. The catalytic reactions were carried out in water as a safe, cheap and green solvent. The catalytic studies indicated that the obtained 1D azido bridged Cu(II) coordination polymer is an active catalyst for preparing β‐hydroxy‐1,2,3‐triazoles. The effect of temperature on the selectivity of the catalytic system was studied and the results indicated this catalytic system has high selectivity at low temperatures. The structure the product obtained from the reaction of 2,3‐epoxypropylphenylether, azide and 1‐ethynyl‐1‐cyclohexanol (T4) was determined by single crystal X‐ray analysis. The results indicate Cu(II) coordination polymers can be a new class of catalytic systems for green click synthesis of 1,2,3‐triazoles.

Synthesis of chiral Cu(II) complexes from pro-chiral Schiff base ligand and investigation of their catalytic activity in the asymmetric synthesis of 1,2,3-triazoles

“…Similar to 1 , the Cu(II) ion is five coordinated in 2 and the CuN 2 OBr 2 coordination environment has distorted square pyramidal geometry with τ = 0.064. The Cu–N and Cu–O bond lengths in the equatorial positions of 2 are close to the similar bonds in 1 (see Table 2 ) and are in the normal range reported in similar Cu(II) complexes 68 – 71 . The Cu–Br1 and Cu–Br2 bond lengths are 2.3602(10) and 2.6607(10) Å, respectively and confirm their coordination to equatorial and axial positions and the presence of Jahn–Teller distortion in the axial direction.…”

Green synthesis of 1,4-disubstituted 1,2,3-triazoles: a sustainable approach

“…This reaction utilized water as the solvent due to its non-toxic properties, cost-effectiveness, and minimal environmental impact. 166 Wang and colleagues presented a MOF that exhibits promising characteristics as a reusable heterogeneous catalyst, capable of efficiently catalyzing click reactions in an aqueous environment, as shown in Table 6, entry (7). 167 Wang et al highlighted a MOF templated Cu(im) 2 derived Cu@N-C catalyst for the one-pot 1,3-dipolar cycloaddition of terminal alkynes, aryl halides and sodium azide in a t-BuOH : H 2 O mixture, yielding 1,4-disubstituted 1,2,3-triazoles with extensive substrate scope and Their study revealed the preparation of diverse 1,2,3-triazoles under solvent-free reaction conditions, achieving good to excellent yields and high selectivity for 1,4-disubstituted 1,2,3-triazoles, as depicted in Table 6, entry (9).…”

Part‐per‐million catalysis of azide‐alkyne cycloaddition reaction in water using a new ferromagnetic μ1,1‐N3 bridged dinuclear Cu(II) complex

“…The first use of Cu(II)-azide complex as a catalyst for such reactions was reported by Noshiranzadeh et al [15] Recently, Bikas et al demonstrated the use of a new azido bridged Cu(II) coordination polymer as a catalyst for green click synthesis of 1,2,3-triazoles. [31] Most recent studies on azido-bridged Cu(II) complexes have focused on their synthesis and magnetic properties. [32][33][34] In general, the azido ligand mediates two types of magnetic coupling (antiferromagnetic or ferromagnetic interactions) depending on its coordination modes (μ 1,1 or μ 1,3 ) and on the structural parameters related to the azido bridges (Cu-N distances and Cu-N-Cu angles).…”

“…The first use of Cu(II)‐azide complex as a catalyst for such reactions was reported by Noshiranzadeh et al [ 15 ] Recently, Bikas et al demonstrated the use of a new azido bridged Cu(II) coordination polymer as a catalyst for green click synthesis of 1,2,3‐triazoles. [ 31 ]…”