PREPARATION AND REACTIONS OF FUNCTIONALIZED BENZYLIC ORGANOMETALLICS OF ZINC AND COPPER

被引：93

作者：

BERK, SC ^{[1
]}

YEH, MCP ^{[1
]}

JEONG, N ^{[1
]}

KNOCHEL, P ^{[1
]}

机构：

[1] UNIV MICHIGAN,DEPT CHEM,ANN ARBOR,MI 48109

来源：

ORGANOMETALLICS | 1990年 / 9卷 / 12期

关键词：

D O I：

10.1021/om00162a016

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of zinc dust with primary or secondary benzylic halides 1 bearing various functional groups such as an ester, halide, cyano, or even a ketone group, in THF or, in the case of benzylic chlorides, in THF:DMSO (4:1), furnishes the corresponding zinc organometallics 2 in high yields. The reaction is accompanied by less than 10% of Wurtz coupling products. The benzylic copper organometallics 3, obtained after a transmetalation of 2 with the THF-soluble copper salt CuCN·2LiCl at -20 °C, react in excellent yields (70-95%) with various electrophiles such as acid chlorides, enones, aldehydes, allylic bromides, ethyl propiolate, and tributyltin chloride, leading to the polyfunctional molecules of type 4. © 1990, American Chemical Society. All rights reserved.

引用

页码：3053 / 3064

页数：12

共 53 条

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