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源自1,3-二氨基胍的单核/双核[VO]/[VO]配合物及其通过氧原子转移催化安息香氧化的应用。

Mononuclear/Binuclear [VO]/[VO] Complexes Derived from 1,3-Diaminoguanidine and Their Catalytic Application for the Oxidation of Benzoin via Oxygen Atom Transfer.

作者信息

Maurya Mannar R, Kumar Naveen, Avecilla Fernando

机构信息

Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee247667, India.

Grupo NanoToxGen, Centro de Investigacións Científicas Avanzadas (CICA), Departamento de Química, Facultade de Ciencias, Universidade da Coruña, Campus de A Coruña, 15071A Coruña, Spain.

出版信息

ACS Omega. 2022 Dec 16;8(1):1301-1318. doi: 10.1021/acsomega.2c06732. eCollection 2023 Jan 10.

DOI:10.1021/acsomega.2c06732
PMID:36643530
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9835170/
Abstract

Ligands Hsal-dag () and HBrsal-dag () derived from 1,3-diaminoguanidine and salicylaldehyde or 5-bromosalicylaldehyde react with one or 2 mol equivalent of vanadium precursor to give two different series of vanadium complexes. Thus, complexes [VO(Hsal-dag) (HO)] () and [VO(HBrsal-dag) (HO)] () were isolated by the reaction of an equimolar ratio of these ligands with [VO(acac)] in MeOH. In the presence of K/Cs ion and using aerially oxidized [VO(acac)], the above reaction gave complexes [K(HO){VO(Hsal-dag)}] (), [Cs(HO){VO(Hsal-dag)}] (), [K(HO){VO(HBrsal-dag)}] (), and [Cs(HO){VO(HBrsal-dag)}] (), which could also be isolated by direct aerial oxidation of complexes and in MeOH in the presence of K/Cs ion. Complexes [(HO)VO(Hsal-dag)VO] () and [(HO)VO(HBrsal-dag)VO] () were isolated upon increasing the ligand-to-vanadium precursor molar ratio to 1:2 under an air atmosphere. When and were reacted with aerially oxidized [VO(acac)] in a 1:2 molar ratio in MeOH in the presence of K/Cs ion, they formed [K(HO){(VO)(Hsal-dag)}] (), [Cs(HO){(VO)(Hsal-dag)}] (), [K(HO){(VO)(Brsal-dag)}] (), and [Cs(HO){(VO)(Brsal-dag)}] (). The structures of complexes , , , and determined by single-crystal X-ray diffraction study confirm the mono-, bi-, tri-, and tetra-anionic behaviors of the ligands. All complexes were found to be an effective catalyst for the oxidation of benzoin to benzil via oxygen atom transfer (OAT) between DMSO and benzoin. Under aerobic condition, this oxidation also proceeds effectively in the absence of DMSO. Electron paramagnetic resonance and V NMR studies demonstrated the active role of a stable V(IV) intermediate during OAT between DMSO and benzoin.

摘要

由1,3 - 二氨基胍与水杨醛或5 - 溴水杨醛衍生而来的配体Hsal - dag（）和HBrsal - dag（）与一摩尔或两摩尔当量的钒前体反应，得到两个不同系列的钒配合物。因此，通过这些配体与[VO(acac)]在甲醇中以等摩尔比反应，分离得到配合物[VO(Hsal - dag)(H₂O)]（）和[VO(HBrsal - dag)(H₂O)]（）。在钾/铯离子存在下并使用空气中氧化的[VO(acac)]，上述反应得到配合物[K(H₂O){VO(Hsal - dag)}]（）、[Cs(H₂O){VO(Hsal - dag)}]（）、[K(H₂O){VO(HBrsal - dag)}]（）和[Cs(H₂O){VO(HBrsal - dag)}]（），它们也可以通过在钾/铯离子存在下在甲醇中直接对配合物和进行空气中氧化而分离得到。在空气气氛下将配体与钒前体的摩尔比增加到1:2时，分离得到配合物[(H₂O)VO(Hsal - dag)VO]（）和[(H₂O)VO(HBrsal - dag)VO]（）。当和在钾/铯离子存在下于甲醇中以1:2的摩尔比与空气中氧化的[VO(acac)]反应时，它们形成[K(H₂O){(VO)₂(Hsal - dag)}]（）、[Cs(H₂O){(VO)₂(Hsal - dag)}]（）、[K(H₂O){(VO)₂(Brsal - dag)}]（）和[Cs(H₂O){(VO)₂(Brsal - dag)}]（）。通过单晶X射线衍射研究确定的配合物、、、的结构证实了配体的单阴离子、双阴离子、三阴离子和四阴离子行为。发现所有配合物都是通过二甲基亚砜（DMSO）与苯偶姻之间的氧原子转移（OAT）将苯偶姻氧化为苯偶酰的有效催化剂。在有氧条件下，在没有DMSO的情况下该氧化反应也能有效进行。电子顺磁共振和钒核磁共振研究表明，在DMSO与苯偶姻之间的OAT过程中，稳定的V(IV)中间体起到了积极作用。

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