Cyanosilylation of Aldehydes Catalyzed by Iron(III) Arylhydrazone-β-Diketone Complexes

被引：38

作者：

Gurbanov, Atash V. ^{[1
,2
]}

Maharramov, Abel M. ^{[2
]}

Zubkov, Fedor I. ^{[3
]}

Saifutdinov, Alexander M. ^{[4
,5
]}

Guseinov, Firudin I. ^{[6
,7
]}

机构：

[1] Univ Lisbon, Inst Super Tecn, Ctr Quim Estrut, Ave Rovisco Pais, P-1049001 Lisbon, Portugal

[2] Baku State Univ, Organ Chem Dept, Z Xalilov St 23, AZ-1148 Baku, Azerbaijan

[3] RUDN Univ, Peoples Friendship Univ Russia, Fac Sci, Organ Chem Dept, 6 Miklukho Maklaya St, Moscow 117198, Russia

[4] Kazan Natl Res Technol Univ, Karl Marx St 68, Kazan 420015, Russia

[5] Immanuel Kant Balt Fed Univ, Inst Chem & Biol, Univ Skaya St, Kaliningrad 236000, Russia

[6] Natl Univ Sci & Technol MISIS, Moscow Leninsky Prospect 4, Moscow 119049, Russia

[7] Russian Acad Sci, Zelinskiy Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2018年 / 71卷 / 2-3期

基金：

俄罗斯科学基金会;

关键词：

METAL-ORGANIC FRAMEWORKS; DICARBOXYL-FUNCTIONALIZED ARYLHYDRAZONE; ASYMMETRIC CYANOHYDRIN SYNTHESIS; TRIMETHYLSILYL CYANIDE ADDITION; HIGHLY EFFICIENT CATALYST; ONE-POT SYNTHESIS; CARBONYL-COMPOUNDS; CU-II; PEROXIDATIVE OXIDATION; RECYCLABLE CATALYST;

D O I：

10.1071/CH17595

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two known iron(III) complexes, [Fe(H2O)(3)(L-1)]center dot xH(2)O (x = 4 (1), 5 (2)) and [Fe(H2O)(3)(L-2)]center dot 3H(2)O (3), bearing the basic forms of 5-chloro-3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxybenzenesulfonic acid (H3L1) and 3-(2-(2,4-dioxopentan-3-ylidene) hydrazinyl)-2-hydroxy-5-nitrobenzenesulfonic acid (H3L2), were prepared and used as homogeneous catalysts for cyanosilylation of a variety of aldehydes with trimethylsilyl cyanide leading to the corresponding cyanohydrin trimethylsilyl ethers. High yield (up to 98 %) was observed in the reaction catalyzed by 3 at room temperature in methanol.

引用

页码：190 / 194

页数：5

共 79 条

[1]

[Anonymous], 2008, J ANAL CHEM+

[2] An improved synthesis of cyanohydrins in the presence of solid LiClO4 under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 688 (1-2) :283-285

[3]

Bandini M, 2002, EUR J ORG CHEM, V2002, P3243

[4] Tuning the catalytic activity of lanthanide-organic framework for the cyanosilylation of aldehydes [J].

Batista, Poliane K. ;

Alves, Danilo J. M. ;

Rodrigues, Marcelo O. ;

de Sa, Gilberto F. ;

Junior, Severino A. ;

Vale, Juliana A. .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2013, 379 :68-71

[5] Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes [J].

Blocka, Ewelina ;

Bosiak, Mariusz J. ;

Welniak, Mirosfaw ;

Ludwiczak, Agnieszka ;

Wojtczak, Andrzej .

TETRAHEDRON-ASYMMETRY, 2014, 25 (6-7) :554-562

[6] Solvent-free heterogeneous catalysis for cyanosilylation in a dynamic cobalt-MOF [J].

Cui, Xin ;

Xu, Mei-Chen ;

Zhang, Ling-Juan ;

Yao, Ru-Xin ;

Zhang, Xian-Ming .

DALTON TRANSACTIONS, 2015, 44 (28) :12711-12716

[7]

Curini M, 1999, SYNLETT, P315

[8] Vanadyl triflate as an efficient and recyclable catalyst for trimethylsilyl cyanide addition to carbonyl compounds [J].

De, SK ;

Gibbs, RA .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 232 (1-2) :123-125

[9] Tetraethylammonium 2-(N-hydroxycarbamoyl)benzoate: a powerful bifunctional metal-free catalyst for efficient and rapid cyanosilylation of carbonyl compounds under mild conditions [J].

Dekamin, Mohammad G. ;

Karimi, Zahra ;

Farahmand, Mehdi .

CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (07) :1375-1381

[10] P(RNCH2CH2)N:: efficient catalysts for the cyanosilylation of aldehydes and ketones [J].

Fetterly, BM ;

Verkade, JG .

TETRAHEDRON LETTERS, 2005, 46 (46) :8061-8066

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