Cp2TiCl/D2O/Mn, a formidable reagent for the deuteration of organic compounds

被引：10

作者：

Rosales, Antonio ^{[1
,2
]}

Rodriguez-Garcia, Ignacio ^{[3
]}

机构：

[1] Univ Seville, Escuela Politecn Super, Dept Chem & Environm Engn, Seville 41011, Spain

[2] Univ Fuerzas Armadas ESPE, Petrochem Engn, Latacunga 050150, Ecuador

[3] Univ Almeria, CeiA3, Quim Organ, Almeria 04120, Spain

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷

关键词：

deuteration; deuterium atom transfer; radical and/or organometallic chemistry; titanocene; HYDROGEN-ATOM SOURCE; D EXCHANGE-REACTION; ELECTRON-TRANSFER; RADICAL CHEMISTRY; STRAIGHTFORWARD SYNTHESIS; SELECTIVE REDUCTION; H/D EXCHANGE; TI-III; DEUTERIUM; COMPLEXES;

D O I：

10.3762/bjoc.12.154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cp2TiCl/D2O/Mn is an efficient combination, sustainable and cheap reagent that mediates the D-atom transfer from D2O to different functional groups and can contribute to the synthesis of new deuterated organic compounds under friendly experimental conditions and with great economic advantages.

引用

页码：1585 / 1589

页数：5

共 38 条

[1] The renaissance of H/D exchange [J].

Atzrodt, Jens ;

Derdau, Volker ;

Fey, Thorsten ;

Zimmermann, Jochen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (41) :7744-7765

[2] Titanocene-catalysed, selective reduction of ketones in aqueous media.: A safe, mild, inexpensive procedure for the synthesis of secondary alcohols via radical chemistry [J].

Barrero, AF ;

Rosales, A ;

Cuerva, JM ;

Gansäuer, A ;

Oltra, JE .

TETRAHEDRON LETTERS, 2003, 44 (05) :1079-1082

[3] Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides.: Straightforward synthesis and absolute stereochemistry of (+)-3α-hydroxyreynosin and related eudesmanolides [J].

Barrero, AF ;

Oltra, JE ;

Cuerva, JM ;

Rosales, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2566-2571

[4] Unprecedented hydrogen transfer from water to alkenes and alkynes mediated by TiIII and late transition metals [J].

Campana, Araceli G. ;

Estevez, Rosa E. ;

Fuentes, Noelia ;

Robles, Rafael ;

Cuerva, Juan M. ;

Bunuel, Elena ;

Cardenas, Diego ;

Oltra, J. Enrique .

ORGANIC LETTERS, 2007, 9 (11) :2195-2198

[5] Water:: The ideal hydrogen-atom source in free-radical chemistry mediated by TiIII and other single-electron-transfer metals? [J].

Cuerva, Juan M. ;

Campana, Araceli G. ;

Justicia, Jose ;

Rosales, Antonio ;

Oller-Lopez, Juan L. ;

Robles, Rafael ;

Cardenas, Diego J. ;

Bunuel, Elena ;

Oltra, J. Enrique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (33) :5522-5526

[6] Reductive C-C bond formation after epoxide opening via electron transfer [J].

Gansaeuer, Andreas ;

Justicia, Jose ;

Fan, Chun-An ;

Worgull, Dennis ;

Piestert, Frederik .

METAL CATALYZED REDUCTIVE C-C BOND FORMATION: A DEPARTURE FROM PREFORMED ORGANOMETALLIC REAGENTS, 2007, 279 :25-52

[7] Catalytic Hydrogen Atom Transfer (HAT) for Sustainable and Diastereoselective Radical Reduction [J].

Gansaeuer, Andreas ;

Klatte, Max ;

Braendle, Gerhard M. ;

Friedrich, Joachim .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (35) :8891-8894

[8] H2O Activation for Hydrogen-Atom Transfer: Correct Structures and Revised Mechanisms [J].

Gansaeuer, Andreas ;

Behlendorf, Maike ;

Cangoenuel, Asli ;

Kube, Christian ;

Cuerva, Juan M. ;

Friedrich, Joachim ;

van Gastel, Maurice .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (13) :3266-3270

[9] Hydrogen Atom Donors: Recent Developments [J].

Gansaeuer, Andreas ;

Shi, Lei ;

Otte, Matthias ;

Huth, Inga ;

Rosales, Antonio ;

Sancho-Sanz, Iris ;

Padial, Natalia M. ;

Enrique Oltra, J. .

RADICALS IN SYNTHESIS III, 2012, 320 :93-120

[10] Strained heterocycles in radical chemistry [J].

Gansäuer, A ;

Lauterbach, T ;

Narayan, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (45) :5556-5573

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