Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides

被引:390
作者
Krasovskiy, Arkady [1 ]
Malakhov, Vladimir [1 ]
Gavryushin, Andrei [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
关键词
coupling; homogeneous catalysis; insertion; organozinc compounds; zinc;
D O I
10.1002/anie.200601450
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Insider dealing: A wide range of poly-functional (hetero)aromatic and aliphatic zinc reagents can be easily prepared in THF. The compounds are formed by a Zn insertion reaction mediated by the addition of LiCl (see scheme; All = allyl). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6040 / 6044
页数:5
相关论文
共 27 条
[1]  
[Anonymous], METAL CATALYZED CROS
[2]   ACTIVATED METALS - PROCEDURE FOR PREPARATION OF ACTIVATED MAGNESIUM AND ZINC [J].
ARNOLD, RT ;
KULENOVIC, ST .
SYNTHETIC COMMUNICATIONS, 1977, 7 (03) :223-232
[3]   New efficient preparation of functionalized arylzinc or thienylzinc compounds from aryl or thienyl chlorides using cobalt catalysis [J].
Gosmini, C ;
Amatore, M ;
Claudel, S ;
Périchon, J .
SYNLETT, 2005, (14) :2171-2174
[4]   Functionalized arylzinc compounds in ethereal solvent: Direct synthesis from aryl iodides and zinc powder and application to Pd-catalyzed reaction with allylic halides [J].
Ikegami, R ;
Koresawa, A ;
Shibata, T ;
Takagi, K .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2195-2199
[5]   New progress in the cobalt-catalysed synthesis of aromatic organozinc compounds by reduction of aromatic halides by zinc dust [J].
Kazmierski, I ;
Gosmini, C ;
Paris, JM ;
Périchon, J .
TETRAHEDRON LETTERS, 2003, 44 (34) :6417-6420
[6]   SYNTHESIS AND REACTIVITY TOWARD ACYL CHLORIDES AND ENONES OF THE NEW HIGHLY FUNCTIONALIZED COPPER REAGENTS RCU(CN)ZNI [J].
KNOCHEL, P ;
YEH, MCP ;
BERK, SC ;
TALBERT, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2390-2392
[7]  
Knochel P., 1999, ORGANOZINC REAGENTS
[8]  
Knochel P., 1994, ORGANOCOPPER REAGENT, P85
[9]  
Knochel P, 2005, HANDBOOK OF FUNCTIONALIZED ORGANOMETALLICS: APPLICATIONS IN SYNTHESIS, P251
[10]   A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides [J].
Krasovskiy, A ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3333-3336