Taming Hazardous Chemistry in Flow: The Continuous Processing of Diazo and Diazonium Compounds

被引:163
作者
Deadman, Benjamin J. [1 ]
Collins, Stuart G. [1 ]
Maguire, Anita R. [1 ,2 ,3 ]
机构
[1] Univ Coll Cork, Dept Chem, Analyt & Biol Chem Res Facil, Synth & Solid State Pharmaceut Ctr, Cork, Ireland
[2] Univ Coll Cork, Dept Chem, Cork, Ireland
[3] Univ Coll Cork, Sch Pharm, Analyt & Biol Chem Res Facil, Synth & Solid State Pharmaceut Ctr, Cork, Ireland
基金
爱尔兰科学基金会;
关键词
continuous processing; diazocarbonyls; diazomethane; diazonium ions; flow chemistry;
D O I
10.1002/chem.201404348
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthetic utilities of the diazo and diazonium groups are matched only by their reputation for explosive decomposition. Continuous processing technology offers new opportunities to make and use these versatile intermediates at a range of scales with improved safety over traditional batch processes. In this minireview, the state of the art in the continuous flow processing of reactive diazo and diazonium species is discussed.
引用
收藏
页码:2298 / 2308
页数:11
相关论文
共 109 条
[1]  
Maas G., Angew. Chem. Int. Ed., 48, pp. 8186-8195, (2009)
[2]  
Angew. Chem., 121, pp. 8332-8341, (2009)
[3]  
Pechmann H.V., Ber. Dtsch. Chem. Ges., 27, pp. 1888-1891, (1894)
[4]  
Corey E.J., Felix A.M., J. Am. Chem. Soc., 87, pp. 2518-2519, (1965)
[5]  
Candeias N.R., Gois P.M.P., Veiros L.F., Afonso C.A.M., J. Org. Chem., 73, pp. 5926-5932, (2008)
[6]  
Ye T., McKervey M.A., Chem. Rev., 94, pp. 1091-1160, (1994)
[7]  
Doyle M.P., Duffy R., Ratnikov M., Zhou L., Chem. Rev., 110, pp. 704-724, (2010)
[8]  
Doyle M.P., McKervey M.A., Ye T., Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, (1998)
[9]  
Slattery C.N., Ford A., Maguire A.R., Tetrahedron, 66, pp. 6681-6705, (2010)
[10]  
Flynn C.J., Elcoate C.J., Lawrence S.E., Maguire A.R., J. Am. Chem. Soc., 132, pp. 1184-1185, (2010)