Arene-catalysed lithiation of triflates and triflamides under Barbier-type conditions: An indirect transformation of alcohols and amines into organolithium compounds

被引：20

作者：

Alonso, E ^{[1
]}

Ramon, DJ ^{[1
]}

Yus, M ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALICANTE,SPAIN

来源：

TETRAHEDRON | 1996年 / 52卷 / 45期

关键词：

D O I：

10.1016/0040-4020(96)00886-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of alkyl triflates 1 or allyl or benzyl triflamides 3 with an excess of lithium powder and a catalytic amount of naphthalene (4 mol %) in the presence of different electrophiles [Me(3)SiCl, (PrCHO)-C-i, Bu(t)CHO, PhCHO, 4-MeOC(6)H(4)CHO, CH3(CH2)(6)CHO, Et(2)CO, (CH2)(5)CO, (c-C3H5)(2)CO, PhCOMe, 4-MeC(6)H(4)COPh, PhCH=NPh, n-C8H7CON(CH2)(4)] in THF at temperature ranging between -78 and 0 degrees C leads, after hydrolysis with water, to the corresponding condensation products 2. When alpha,beta-unsaturated carbonyl compounds are used as electrophilic compounds 1,2-(2-cyclohexenone) or 1,4-addition (cinnamaldehyde or benzylideneacetone) takes places depending on the electrophile used. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：14341 / 14348

页数：8

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