Taking up the cudgels for perchlorates: Uses and applications in organic reactions under mild conditions

被引:22
作者
Bartoli, Giuseppe [1 ]
Locatelli, Manuela [1 ]
Melchiorre, Paolo [1 ]
Sambri, Letizia [1 ]
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
关键词
Lewis acids; organic syntheses; perchlorates; safety;
D O I
10.1002/ejoc.200600852
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Metal perchlorates are compounds of great chemical interest since they possess some unique properties, such as high electronegativity and relatively low charge density, poor complexing ability, high solubility in various organic solvents, and kinetic stability under mild conditions. Besides providing polar media when dissolved in solvents, metal perchlorates have recently found wide employment as Lewis acid promoters in various organic transformations, both in the development of new techniques for known and widely used reactions and in promotion of new kinds of reactivity. This paper presents a general overview of the more recent uses of lithium, magnesium, zinc, and nickel perchlorates, underlining the fact that such perchlorates are quite safe chemical products under mild conditions. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
引用
收藏
页码:2037 / 2049
页数:13
相关论文
共 81 条
[1]  
Anastas PT., 1998, Principles of green chemistry
[2]   LiClO4•3H2O promoted highly regioselective ring-opening of epoxides with thiols under neutral conditions [J].
Azizi, N ;
Saidi, MR .
CATALYSIS COMMUNICATIONS, 2006, 7 (04) :224-227
[3]   Solid lithium perchlorate as a powerful catalyst for the synthesis of β-aminoalcohols under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (05) :505-507
[4]   LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
TETRAHEDRON, 2004, 60 (02) :383-387
[5]   Lithium perchlorate-catalyzed three-component coupling:: A facile and general method for the synthesis of α-aminophosphonates under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4630-4633
[6]   A novel procedure for conversion of epoxides to α-hydroxyphosphonates with a trialkylphosphite mediated by LiClO4 [J].
Azizi, N ;
Said, MR .
TETRAHEDRON LETTERS, 2003, 44 (43) :7933-7935
[7]   Highly efficient solvent-free condensation of carboxylic acids with alcohols catalysed by zinc perchlorate hexahydrate, Zn(CIO4)2•6 H2O [J].
Bartoli, G ;
Boeglin, J ;
Bosco, M ;
Locatelli, M ;
Massaccesi, M ;
Melchiorre, P ;
Sambri, L .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (01) :33-38
[8]   Unusual and unexpected reactivity of t-butyl dicarbonate (Boc2O)with alcohols in the presence of magnesium perchlorate.: A new and general route to t-butyl ethers [J].
Bartoli, G ;
Bosco, M ;
Locatelli, M ;
Marcantoni, E ;
Melchiorre, P ;
Sambri, L .
ORGANIC LETTERS, 2005, 7 (03) :427-430
[9]   A Lewis acid-mediated protocol for the protection of aryl amines as their Boc-derivatives [J].
Bartoli, G ;
Bosco, M ;
Locatelli, M ;
Marcantoni, E ;
Massaccesi, M ;
Melchiorre, P ;
Sambri, L .
SYNLETT, 2004, (10) :1794-1798
[10]   Zn(ClO4)2•6H2O as a powerful catalyst for the conversion of β-ketoesters into β-enamino esters [J].
Bartoli, G ;
Bosco, M ;
Locatelli, M ;
Marcantoni, E ;
Melchiorre, P ;
Sambri, L .
SYNLETT, 2004, (02) :239-242