Revisiting nucleophilic substitution reactions: Microwave-assisted synthesis of azides, thiocyanates, and sulfones in an aqueous medium

被引:192
作者
Ju, Yuhong
Kumar, Dalip
Varma, Rajender S.
机构
[1] US EPA, Clean Proc Branch, Sustainable Technol Div, Natl Risk Management Res Lab, Cincinnati, OH 45268 USA
[2] Birla Inst Technol & Sci, Chem Grp, Pilani 333031, Rajasthan, India
关键词
D O I
10.1021/jo061114h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical, rapid, and efficient microwave ( MW) promoted synthesis of various azides, thiocyanates, and sulfones is described in an aqueous medium. This general and expeditious MW-enhanced nucleophilic substitution approach uses easily accessible starting materials such as halides or tosylates in reaction with alkali azides, thiocyanates, or sulfinates in the absence of any phase-transfer catalyst, and a variety of reactive functional groups are tolerated.
引用
收藏
页码:6697 / 6700
页数:4
相关论文
共 47 条
[41]   Solvent-free organic syntheses - using supported reagents and microwave irradiation [J].
Varma, RS .
GREEN CHEMISTRY, 1999, 1 (01) :43-55
[42]   Can ultrasound substitute for a phase-transfer catalyst?: Triphase catalysis and sonochemical acceleration in nucleophilic substitution of alkyl halides and α-tosyloxyketones:: synthesis of alkyl azides and α-azidoketone [J].
Varma, RS ;
Naicker, KP ;
Kumar, D .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 149 (1-2) :153-160
[43]   Surfactant pillared clays in phase transfer catalysis: A new route to alkyl azides from alkyl bromides and sodium azide [J].
Varma, RS ;
Naicker, KP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2915-2918
[44]   A facile preparation of alkyl azides from alkyl bromides and sodium azide using 18-crown-6 ether doped clay [J].
Varma, RS ;
Naicker, KP ;
Aschberger, J .
SYNTHETIC COMMUNICATIONS, 1999, 29 (16) :2823-2830
[45]  
VARMA RS, 2004, KIRKOTHMER ENCY CHEM
[46]  
VARMA RS, 2002, SADV GREEN CHEM CHEM
[47]   Water as a reaction medium for clean chemical processes [J].
Wu Wei ;
Charlene C. K. Keh ;
Chao-Jun Li ;
Rajender S. Varma .
Clean Technologies and Environmental Policy, 2004, 7 (1) :62-69