Copper(I) complexes with heteroaromatic hydrazone ligands: Synthesis, crystal structure and catalytic insights for tetrazole synthesis

IF 2.7 3区化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR

Inorganica Chimica Acta Pub Date : 2024-10-29 DOI:10.1016/j.ica.2024.122418

S. Gayathri , P. Viswanathamurthi , J.G. Malecki , A. Bhavadharini , K. Senthilkumar

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引用次数: 0

Abstract

The reaction between [Cu(PPh₃)₂(CH₃COO)] and hydrazone ligands derived from heteroaromatics (L_1-3) [L₁ = 2-(2-benzothiazole-2-yl)hydrazineylidene)acenaphthylen-1-one, L₂ = 2-(2-isoquinolin-3-yl)hydrazineylidene)acenaphthylen-1-one, L₃ = 2-(2-oxoacenaphthylen-1-ylidene)hydrazineyl)nicotinic acid] gives rise to a novel series of Cu(I) complexes of the type [Cu(PPh₃)₂(L_1-3)]. The structural confirmation of these complexes has been achieved through comprehensive analysis utilizing FT-IR, UV–Vis, NMR, and ESI-MS techniques. By utilizing single crystal X-ray diffraction, it has been established that the copper(I) ion is surrounded by a tetrahedral geometry, and a Schiff base is bound to it via a bidentate N^N coordination mode. These newly synthesized copper complexes exhibit excellent catalytic activity in three components reactions, involving diverse aldehydes, hydroxylamine hydrochloride, and sodium azide, leading to the production of variety of tetrazole derivatives. Remarkably, using 1.0 mol % of Cu(I) catalyst loading and an oxygen (O₂) environment, a vast diversity of substituted tetrazoles have been efficiently synthesized with yields ranging from good to outstanding.

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杂芳香族腙配体的铜（I）配合物：四氮唑合成、晶体结构和催化见解

Cu(PPh3)2(CH3COO)]和来自杂芳烃的腙配体（L1-3）[L1 = 2-(2-苯并噻唑-2-基)肼亚基)苊-1-酮、L2 = 2-(2-异喹啉-3-基)肼亚基)苊烯-1-酮，L3 = 2-(2-氧代苊烯-1-亚基)肼亚基)烟酸]产生了一系列新的[Cu(PPh3)2(L1-3)]型 Cu(I)配合物。利用傅立叶变换红外光谱（FT-IR）、紫外可见光谱（UV-Vis）、核磁共振（NMR）和电离质谱（ESI-MS）技术进行综合分析，确认了这些配合物的结构。通过利用单晶 X 射线衍射，确定了铜（I）离子被四面体几何结构包围，并通过双齿 N^N 配位模式与希夫碱结合。这些新合成的铜配合物在涉及多种醛类、盐酸羟胺和叠氮化钠的三组分反应中表现出卓越的催化活性，从而生成了多种四氮唑衍生物。值得注意的是，使用 1.0 mol % 的 Cu(I) 催化剂负载和氧气（O2）环境，可以高效合成多种取代的四唑，产量从良好到卓越不等。

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来源期刊

Inorganica Chimica Acta 化学-无机化学与核化学

CiteScore

6.00

自引率

3.60%

发文量

440

审稿时长

35 days

期刊介绍： Inorganica Chimica Acta is an established international forum for all aspects of advanced Inorganic Chemistry. Original papers of high scientific level and interest are published in the form of Articles and Reviews. Topics covered include: • chemistry of the main group elements and the d- and f-block metals, including the synthesis, characterization and reactivity of coordination, organometallic, biomimetic, supramolecular coordination compounds, including associated computational studies; • synthesis, physico-chemical properties, applications of molecule-based nano-scaled clusters and nanomaterials designed using the principles of coordination chemistry, as well as coordination polymers (CPs), metal-organic frameworks (MOFs), metal-organic polyhedra (MPOs); • reaction mechanisms and physico-chemical investigations computational studies of metalloenzymes and their models; • applications of inorganic compounds, metallodrugs and molecule-based materials. Papers composed primarily of structural reports will typically not be considered for publication.