Synthesis of functionalized nitroarylmagnesium halides via an iodine-magnesium exchange

被引:47
作者
Sapountzis, L [1 ]
Dube, H [1 ]
Lewis, R [1 ]
Gommermann, N [1 ]
Knochel, P [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
关键词
D O I
10.1021/jo048132o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various nitro-substituted aryl and heteroaryl iodides undergo an iodine-magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures below -40 degrees C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.
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页码:2445 / 2454
页数:10
相关论文
共 79 条
[1]   The directed ortho metalation -: cross coupling symbiosis.: Regioselective methodologies for biaryls and heterobiaryls.: Deployment in aromatic and heteroaromatic natural product synthesis [J].
Anctil, EJG ;
Snieckus, V .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) :150-160
[2]  
[Anonymous], 1954, GRIGNARD REACTIONS N
[3]  
ASHWOOD MS, 1988, SYNTHESIS-STUTTGART, P379
[4]  
BAIK WP, 2002, Patent No. 2001KR1586
[5]   THE REACTION OF VINYL GRIGNARD-REAGENTS WITH 2-SUBSTITUTED NITROARENES - A NEW APPROACH TO THE SYNTHESIS OF 7-SUBSTITUTED INDOLES [J].
BARTOLI, G ;
PALMIERI, G ;
BOSCO, M ;
DALPOZZO, R .
TETRAHEDRON LETTERS, 1989, 30 (16) :2129-2132
[6]   CONJUGATE ADDITION OF ALKYL-GRIGNARD REAGENTS TO MONONITROARENES [J].
BARTOLI, G .
ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (03) :109-115
[7]  
Bondoch J., 1997, J AM CHEM SOC, V119, P7230
[8]  
Bonnet V, 2002, SYNLETT, P1008
[9]  
Boymond L, 1998, ANGEW CHEM INT EDIT, V37, P1701, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1701::AID-ANIE1701>3.0.CO
[10]  
2-U