DTBB-catalysed lithiation of chlorinated benzylic chlorides, alcohols, thiols or amines

被引：26

作者：

Gómez, C ^{[1
]}

Huerta, FF ^{[1
]}

Yus, M ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(97)10402-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of chlorinated benzyl chlorides (1) with an excess of lithium powder and a catalytic amount of DTBB (4 mol %) in the presence of different electrophiles [(PrCHO)-C-i, (BuCHO)-C-t, Et2CO, (CH2)(5)CO, PhCOMe, Me3SiCl] in THF at -50 degrees C followed by hydrolysis with water leads to the corresponding compounds 2. When the same DTBB-catalysed lithiation is applied to several chlorinated benzylic alcohols or mercaptans (4 or 5) it is necessary to deprotonate the starting material with (BuLi)-Li-n; treatment of the resulting anions or amine 6 as above, but at -78 degrees C, leads to the expected reaction products 8, after reaction with different electrophiles [(PrCHO)-C-i, (BuCHO)-C-t, Et2CO, (CH2)(5)CO, PhCOMe, Me2SiCl] and fnal hydrolysis with water. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1853 / 1866

页数：14