Power ultrasound in metal-assisted synthesis: From classical Barbier-like reactions to click chemistry

被引:60
作者
Cintas, Pedro [3 ]
Palmisano, Giovanni [2 ]
Cravotto, Giancarlo [1 ]
机构
[1] Univ Turin, Dipartimento Sci & Tecnol Farmaco, I-10235 Turin, Italy
[2] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
[3] Univ Extremadura, Dept Quim Organ & Inorgan, E-06006 Badajoz, Spain
关键词
Power ultrasound; Metal-assisted synthesis; Barbier-like reactions; Click reactions; Combined ultrasound/microwave irradiation; ORGANIC-SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; SONOCHEMICAL SYNTHESIS; CARBONYL-COMPOUNDS; TERMINAL ALKYNES; REAGENTS; INDIUM; FACILE; ACCESS; ALLYLATION;
D O I
10.1016/j.ultsonch.2010.11.020
中图分类号
O42 [声学];
学科分类号
070206 ; 082403 ;
摘要
The search for more efficient and greener synthetic procedures to obtain highly functionalized chemical structures has always found in metal-assisted reactions a noteworthy strategy. All these reactions fall in the main domain of sonochemistry; in fact few techniques can compete with power ultrasound in so efficiently activating a metal surface, thus enhancing and accelerating its subsequent reaction with an organic substrate. Young researchers will certainly benefit from the rich literature and past experience of several pioneers who have, since the early eighties, laid the foundations of modern sonochemical synthetic protocols. Herein we provide a concise overview that describes how ultrasound acts in such a way as to make it a fundamental tool in improving the classical one-step coupling promoted by zero-valent metal species, usually referred to as Barbier-like reactions. From early hallmarks to recent accomplishments, especially the latest Cu-catalyzed alkyne-azide reaction (the so-called Click reaction), intended to be a universal ligation in chemistry and biology; we highlight the role and crucial effects of sonication on these processes. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:836 / 841
页数:6
相关论文
共 54 条
[41]  
Mason T.J., 2002, SYNTHESIS, V61
[42]   ALLYLZINC REAGENT ADDITIONS IN AQUEOUS-MEDIA [J].
PETRIER, C ;
LUCHE, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :910-912
[43]   ULTRASOUND IN ORGANIC-SYNTHESIS .7. PREPARATION OF ORGANOZINC REAGENTS AND THEIR NICKEL-CATALYZED REACTIONS WITH ALPHA, BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
PETRIER, C ;
BARBOSA, JCD ;
DUPUY, C ;
LUCHE, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5761-5765
[44]  
Rayleigh L., 1917, London Edinburgh Dublin Phil. Mag. J. Sci., V34, P94, DOI DOI 10.1080/14786440808635681
[45]  
RENAUD P, 1950, B SOC CHIM FR, V17, P1044
[46]  
Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO
[47]  
2-4
[48]  
Shih-Yuan A., 1996, TETRAHEDRON LETT, V37, P495
[49]   Sonochemical synthesis of 1,4-disubstituted 1,2,3-triazoles in aqueous medium [J].
Sreedhar, B. ;
Reddy, P. Surendra .
SYNTHETIC COMMUNICATIONS, 2007, 37 (4-6) :805-812
[50]  
Suslick K.S., 1990, ADV SONOCHEM, V1, P197