PREPARATION OF NEW CLASSES OF ALIPHATIC, ALLYLIC, AND BENZYLIC ZINC AND COPPER REAGENTS BY THE INSERTION OF ZINC DUST INTO ORGANIC HALIDES, PHOSPHATES, AND SULFONATES

被引:112
作者
JUBERT, C
KNOCHEL, P
机构
[1] ROUSSEL UCLAF,CTR RECH,F-93230 ROMAINVILLE,FRANCE
[2] UNIV MICHIGAN,WILLARD H DOW LABS,DEPT CHEM,ANN ARBOR,MI 48109
关键词
D O I
10.1021/jo00046a026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The insertion of zinc dust into primary alkyl chlorides, bromides, phosphates, and sulfonates in a polar solvent (DMPU, DMA) and in the presence of a catalytic amount of LiI (0.2 equiv) provides new organozinc reagents of the type RZnX (X = Cl, Br, OSO2R, OP(O)(OR)2) in excellent yields. After the transmetalation to the corresponding copper reagent RCu(CN)ZnX using CuCN.2LiCl, the addition of electrophiles, such as Michael acceptors, affords the desired adducts. Similarly, various new allylic and benzylic zinc reagents were prepared without the formation of any Wurtz-coupling side product and reacted with various electrophiles.
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页码:5425 / 5431
页数:7
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