Mild and Selective Heterogeneous Catalytic Hydration of Nitriles to Amides by Flowing through Manganese Dioxide

被引：111

作者：

Battilocchio, Claudio ^{[1
]}

Hawkins, Joel M. ^{[2
]}

Ley, Steven V. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England

[2] Pfizer Worldwide Res & Dev, Groton, CT 06340 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 04期

关键词：

EFFICIENT HYDRATION; NATURAL PHOSPHATE; AQUEOUS-MEDIUM; WATER; CHEMISTRY; OXIDATION; HYDROXYAPATITE; HYDROLYSIS; REACTORS; COMPLEX;

D O I：

10.1021/ol403591c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sustainable flow chemistry process for the hydration of nitrites, whereby an aqueous solution of the nitrite is passed through a column containing commercially available amorphous manganese dioxide, has been developed. The product is obtained simply by concentration of the output stream without any other workup steps. The protocol described is rapid, robust, reliable, and scalable, and it has been applied to a broad range of substrates, showing a high level of chemical tolerance.

引用

收藏

页码：1060 / 1063

页数：4

相关论文

共 56 条

[1] Investigation of the Reactivity of Pt Phosphinito and Molybdocene Nitrile Hydration Catalysts With Cyanohydrins [J].

Ahmed, Takiya J. ;

Fox, Brandy R. ;

Knapp, Spring Melody M. ;

Yelle, Robert B. ;

Juliette, J. Jerrick ;

Tyler, David R. .

INORGANIC CHEMISTRY, 2009, 48 (16) :7828-7837

[2] A facile one-pot synthesis of ruthenium hydroxide nanoparticles on magnetic silica: aqueous hydration of nitriles to amides [J].

Baig, R. B. Nasir ;

Varma, Rajender S. .

CHEMICAL COMMUNICATIONS, 2012, 48 (50) :6220-6222

[3]

Bailey P.D., 2005, Comprehensive Organic Functional Group Transformations II, V5, P201

[4] A Machine-Assisted Flow Synthesis of SR48692: A Probe for the Investigation of Neurotensin Receptor-1 [J].

Battilocchio, Claudio ;

Deadman, Benjamin J. ;

Nikbin, Nikzad ;

Kitching, Matthew O. ;

Baxendale, Ian R. ;

Ley, Steven V. .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (24) :7917-7930

[5] A Mild and Efficient Flow Procedure for the Transfer Hydrogenation of Ketones and Aldehydes using Hydrous Zirconia [J].

Battilocchio, Claudio ;

Hawkins, Joel M. ;

Ley, Steven V. .

ORGANIC LETTERS, 2013, 15 (09) :2278-2281

[6] Azide monoliths as convenient flow reactors for efficient Curtius rearrangement reactions [J].

Baumann, Marcus ;

Baxendale, Ian R. ;

Ley, Steven V. ;

Nikbin, Nikzad ;

Smith, Christopher D. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) :1587-1593

[7] Total synthesis of the amaryllidaceae alkaloid (+)-plicamine using solid-supported reagents [J].

Baxendale, IR ;

Ley, SV ;

Nessi, M ;

Piutti, C .

TETRAHEDRON, 2002, 58 (32) :6285-6304

[8] A facile synthesis of amides by selective hydration of nitriles using modified natural phosphate and hydroxyapatite as new catalysts [J].

Bazi, F ;

El Badaoui, H ;

Tamani, S ;

Sokori, S ;

Solhy, A ;

Macquarrie, DJ ;

Sebti, S .

APPLIED CATALYSIS A-GENERAL, 2006, 301 (02) :211-214

[9] Organometallic chemistry in aqueous solution.: Hydration of nitriles to amides catalyzed by a water-soluble molybdocene, (MeCp)2Mo(OH)(H2O)+ [J].

Breno, KL ;

Pluth, MD ;

Tyler, DR .

ORGANOMETALLICS, 2003, 22 (06) :1203-1211

[10] A MILD HYDRATION OF NITRILES INTO AMIDES [J].

BREUILLES, P ;

LECLERC, R ;

UGUEN, D .

TETRAHEDRON LETTERS, 1994, 35 (09) :1401-1404

← 1 2 3 4 5 6 →