Diorganyl diselenides: a powerful tool for the construction of selenium containing scaffolds

被引：43

作者：

Sonawane, Amol D. ^{[1
]}

Sonawane, Rohini A. ^{[1
]}

Ninomiya, Masayuki ^{[1
]}

Koketsu, Mamoru ^{[1
]}

机构：

[1] Gifu Univ, Dept Chem & Biomol Sci, Fac Engn, 1-1 Yanagido, Gifu 5011193, Japan

来源：

DALTON TRANSACTIONS | 2021年 / 50卷 / 37期

关键词：

COPPER-CATALYZED SYNTHESIS; C-H CHALCOGENATION; UNSYMMETRICAL DIARYL SELENIDES; CROSS-COUPLING REACTIONS; ELECTROCHEMICAL OXIDATIVE CYCLIZATION; METAL-FREE CHALCOGENATION; ONE-POT SYNTHESIS; ARYLBORONIC ACIDS; TRANSITION-METAL; ARYL HALIDES;

D O I：

10.1039/d1dt01982a

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Organoselenium compounds find versatile applications in organic synthesis, materials synthesis, and ligand chemistry. Organoselenium heterocycles are widely studied agents with diverse applications in various biological processes. This review highlights the recent progress in the synthesis of selenium heterocycles using diorganyl diselenides with keen attention on green synthetic approaches, scopes, C-H selanylation, the mechanisms of different reactions and insights into the formation of metal complexes. The C-H selanylation using diorganyl diselenides with different catalysts, bases, transition metals, iodine salts, NIS, hypervalent iodine, and other reagents is summarised. Finally, the diverse binding modes of bis(2/4-pyridyl)diselenide with different metal complexes are also summarised.

引用

页码：12764 / 12790

页数：27

共 187 条

[11] Recent developments in the synthesis of biologically relevant selenium-containing scaffolds [J].

Banerjee, Bubun ;

Koketsu, Mamoru .

COORDINATION CHEMISTRY REVIEWS, 2017, 339 :104-127

[12] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[13] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[14] NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions [J].

Bettanin, Luana ;

Saba, Sumbal ;

Doerner, Carlos, V ;

Franco, Marcelo S. ;

Godoi, Marcelo ;

Rafique, Jamal ;

Braga, Antonio L. .

TETRAHEDRON, 2018, 74 (29) :3971-3980

[15] Addition-Elimination or Nucleophilic Substitution? Understanding the Energy Profiles for the Reaction of Chalcogenolates with Dichalcogenides [J].

Bortoli, Marco ;

Wolters, Lando P. ;

Orian, Laura ;

Bickelhaupt, F. Matthias .

JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2016, 12 (06) :2752-2761

[16] Coordination chemistry and synthetic approaches of pyridyl-selenium ligands: A decade update [J].

Cargnelutti, Roberta ;

Schumacher, Ricardo F. ;

Belladona, Andrei L. ;

Kazmierczak, Jean C. .

COORDINATION CHEMISTRY REVIEWS, 2021, 426

[17] Synthesis and structure of Au(I), Cu(I) and Cu(II) complexes with bis(2-pyridyl)diselenide: The copper complexes and its oxidation products [J].

Cargnelutti, Roberta ;

Hagenbach, Adelheid ;

Abram, Ulrich ;

Burrow, Robert A. ;

Lang, Ernesto Schulz .

POLYHEDRON, 2015, 96 :33-37

[18] Synthesis and structure of [ReOSe(2-Se-py)3]: A rhenium(V) complex with selenium(0) as a ligand [J].

Cargnelutti, Roberta ;

Lang, Ernesto S. ;

Piquini, Paulo ;

Abram, Ulrich .

INORGANIC CHEMISTRY COMMUNICATIONS, 2014, 45 :48-50

[19] Iron(III)-catalyzed synthesis of selenoesters from α-amino carbonyl derivatives at room temperature [J].

Chatterjee, Rana ;

Mukherjee, Anindita ;

Santra, Sougata ;

Zyryanov, Grigory, V ;

Majee, Adinath .

TETRAHEDRON, 2019, 75 (43)

[20] Solvent-Controlled Halo-Selective Selenylation of Aryl Halides Catalyzed by Cu(II) Supported on Al2O3. A General Protocol for the Synthesis of Unsymmetrical Organo Mono- and Bis-Selenides [J].

Chatterjee, Tanmay ;

Ranu, Brindaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) :7145-7153

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