Tropylium-BF4 as Organocatalyst for Efficient Synthesis of Nitriles from Aldoximes; Synthetic Scope and Mechanistic Insights

被引：6

作者：

Anchi, Athmanand ^{[1
]}

Sutar, Suraj M. ^{[1
]}

Kalkhambkar, Rajesh G. ^{[1
]}

Borosky, Gabriela L. ^{[2
,3
]}

Laali, Kenneth K. ^{[4
]}

机构：

[1] Karnatak Univ, Karnatak Sci Coll, Dept Chem, Dharwad 580001, Karnataka, India

[2] Univ Nacl Cordoba, INFIQC, CONICET, Fac Ciencias Quim, Ciudad Univ, RA-5000 Cordoba, Argentina

[3] Univ Nacl Cordoba, Dept Quim Teor & Computac, Fac Ciencias Quim, Ciudad Univ, RA-5000 Cordoba, Argentina

[4] Univ North Florida, Dept Chem, 1 UNF Dr, Jacksonville, FL 32224 USA

来源：

CHEMISTRYSELECT | 2022年 / 7卷 / 35期

关键词：

Aldoxime to Nitrile; DFT Computations; Ionic Liquids; Organocatalyst; Tropylium; FACILE SYNTHESIS; IONIC LIQUIDS;

D O I：

10.1002/slct.202202791

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Structurally diverse aldoximes were conveniently transformed within minutes to the corresponding nitriles by using tropylium BF4 as organocatalyst, in 1-butyl-3-methylimidazolium ionic liquids (BMIM-ILs) as solvent, under microwave irradiation. The scope of this convenient, cyanide free, process for nitrile synthesis was explored, and DFT computations were employed to shed light on the mechanistic steps of this catalytic reaction leading to dehydration.

引用

页数：9

共 37 条

[1] Building Heterocyclic Systems with RC(OR)2+ Carbocations in Recyclable Bronsted Acidic Ionic Liquids: Facile Synthesis of 1-Substituted 1H-1,2,3,4-Tetrazoles, Benzazoles and Other Ring Systems with CH(OEt)3 and EtC(OEt)3 in [EtNH3][NO3] and [PMIM(SO3H)][OTf] [J].

Aridoss, Gopalakrishnan ;

Laali, Kenneth K. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (15) :2827-2835

[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3] Tropylium-promoted Ritter reactions [J].

Doan, Son H. ;

Hussein, Mohanad A. ;

Nguyen, Thanh Vinh .

CHEMICAL COMMUNICATIONS, 2021, 57 (71) :8901-8904

[4] Nitrile Synthesis with Aldoxime Dehydratases: A Biocatalytic Platform with Applications in Asymmetric Synthesis, Bulk Chemicals, and Biorefineries [J].

Dominguez de Maria, Pablo .

MOLECULES, 2021, 26 (15)

[5] CYANATION OF AROMATIC HALIDES [J].

ELLIS, GP ;

ROMNEYALEXANDER, TM .

CHEMICAL REVIEWS, 1987, 87 (04) :779-794

[6]

Fatiadi A.J., 1983, Preparation and Synthetic Applications of Cyano Compounds

[7]

Friedrich K., 1970, The Chemistry of the Cyano Group

[8]

Frisch M. J., 2013, GAUSSIAN09 REVISION

[9] THE PATH OF CHEMICAL-REACTIONS - THE IRC APPROACH [J].

FUKUI, K .

ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (12) :363-368

[10]

Grimme S., 2010, J CHEM PHYS, V132, DOI DOI 10.1063/1.3382344

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