Alkali-metal mediated zincation of N-heterocyclic substrates using the lithium zincate complex, (THF)Li(TMP)Zn(tBu)2 and applications in in situ cross coupling reactions

被引：25

作者：

Blair, Victoria L. ^{[1
]}

Blakemore, David C. ^{[2
]}

Hay, Duncan ^{[2
]}

Hevia, Eva ^{[1
]}

Pryde, David C. ^{[2
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland

[2] Pfizer Global Res & Dev, Sandwich Labs, Worldwide Med Chem, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 36期

基金：

英国工程与自然科学研究理事会;

关键词：

Metallation; Zincation; N-Heterocycles; Lithium; Mixed-metal reagents; DIRECTED ORTHO-METALATION; STRUCTURAL BASIS; MAGNESIUM; LITHIATION; BASES; FUNCTIONALIZATION; AROMATICS; EFFICIENT; DIAZINES; AMIDES;

D O I：

10.1016/j.tetlet.2011.06.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study investigates the ability of the mixed-metal reagent [Li(TMP)Zn(tBu)(2)] 1 to promote direct Zn-H exchange reactions (zincations) of a wide range of N-heterocyclic molecules. The generated metallated intermediates from these reactions are intercepted with I-2 and some of them are also employed as precursors in Pd-catalysed Negishi cross-coupling applications. A comparison with recent precedents in metallation chemistry reveals that for some of these heterocycles, 1 allows improved conversions, under milder conditions and in certain cases, even gives unique regioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4590 / 4594

页数：5

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