DIRECT FORMATION OF (HALOARYL)COPPER NUCLEOPHILES FROM HALOIODOBENZENES AND ACTIVE COPPER

被引:11
作者
EBERT, GW
PFENNIG, DR
SUCHAN, SD
DONOVAN, TA
AOUAD, E
TEHRANI, SS
GUNNERSEN, JN
DONG, LM
机构
[1] Department of Chemistry, State University of New York College, Buffalo, New York 14222, Buffalo
关键词
D O I
10.1021/jo00113a013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(o-Halophenyl)-; (m-halophenyl)-, and (p-halophenyl)copper reagents have been formed in moderate to high yields at room temperature from active copper and the corresponding haloiodobenzenes. These reagents have been cross-coupled with a variety of alkyl and acyl halides to produce the respective haloarenes and haloaryl ketones. Remarkably, (o-fluorophenyl)- and (o-chlorophenyl)copper are produced in good yields by this procedure without undergoing elimination to form benzyne making this approach a convenient method for generating o-halophenyl nucleophiles.
引用
收藏
页码:2361 / 2364
页数:4
相关论文
共 46 条
[1]  
Tripathi R.S., Singh H.K., Saxena A.K., Indian J. Chem., Sect. B, 29B, 9, (1990)
[2]  
Bruns R.F., Fergus J.H., Coughenour L.L., Courtland G.G., Pugsley T.A., Dodd J.H., Tinney F.J., Mol. Pharmacol., 38, (1990)
[3]  
March J., Advanced Organic Chemistry Reactions, Mechanisms, and Structure, pp. 534-542, (1992)
[4]  
Corey E.J., Katzenellenbogen J.A., Posner G.H., J. Am. Chem. Soc., 89, (1967)
[5]  
Corey E.J., Katzenellenbogen J.A., Roman S.A., Gilman H.W., Tetrahedron Lett., (1971)
[6]  
Posner G.H., Org. React., 22, (1975)
[7]  
Lipshutz B.H., Wilhelm R.S., Kozlowski J.A., Tetrahedron, 40, (1984)
[8]  
Lipshutz B.H., Synthesis, (1987)
[9]  
Wechter W.J., Slomp G., MacKellar F.A., Wiechart R., Kerb U., Tetrahedron, 21, (1965)
[10]  
Atwater N.W., Bible R.H., Brown E.A., Burtner R.R., Mihina J.S., Nysted L.N.T., Soliman P.B., J. Org. Chem., 26, (1961)