Alkali-metal-mediated zineation of ferrocene: Synthesis, structure, and reactivity of a lithium tmp/zincate reagent

被引：80

作者：

Barley, HRL ^{[1
]}

Clegg, W

Dale, SH

Hevia, E

Honeyman, GW

Kennedy, AR

Mulvey, RE

机构：

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

[2] Newcastle Univ, Sch Nat Sci Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 37期

关键词：

amides; ferrocene; metalation; synergy; zinc;

D O I：

10.1002/anie.200501560

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Deprotonative metalation of ferrocene by a lithium zincate reagent was carried out to form the neutral zinc complex [(Fc)2Zn(tmeda)] and the anionic zincate [Li(thf)4][(Fc) 3Zn] (see scheme; tmp = 2,2,6,6-tetramethylpiperidine, TMEDA = N,N,N′,N′-tetramethylethylenediamine). A 1:1:1 mixture of TMEDA, Li(tmp), and nBu2Zn is used to readily prepare the lithium zincate reagent [LinBu2Zn(tmp)(tmeda)] in situ. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6018 / 6021

页数：4

共 24 条

[1] Sodium dialkyl-amidozincates: Alkyl or amido bases? An experimental and theoretical case study [J].

Andrikopoulos, PC ;

Armstrong, DR ;

Barley, HRL ;

Clegg, W ;

Dale, SH ;

Hevia, E ;

Honeyman, GW ;

Kennedy, AR ;

Mulvey, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6184-6185

[2] BUTYLLITHIUM CUBANE TETRAMERS LINKED BY LI-TMEDA-LI BRIDGES IN AN INFINITE, ZIGZAG CHAIN ARRANGEMENT - 1ST-CRYSTALLOGRAPHIC STUDY OF A SIMPLE BUTYL COMPOUND OF AN EARLY MAIN GROUP ELEMENT [J].

BARNETT, NDR ;

MULVEY, RE ;

CLEGG, W ;

ONEIL, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1573-1574

[3] Hetero-aggregate compounds of aryl and alkyl lithium reagents: A structurally intriguing aspect of organolithium chemistry [J].

Gossage, RA ;

Jastrzebski, JTBH ;

van Koten, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) :1448-1454

[4]

GOSSAGE RA, 2005, ANGEW CHEM, V117, P1472

[5] NOVEL METHOD FOR GENERATION OF SECONDARY ORGANOZINC REAGENT - APPLICATION TO TANDEM CARBON-CARBON BOND FORMATION REACTION OF 1,1-DIBROMOALKANE [J].

HARADA, T ;

KOTANI, Y ;

KATSUHIRA, T ;

OKU, A .

TETRAHEDRON LETTERS, 1991, 32 (12) :1573-1576

[6] General method for preparation of allenic zinc reagents by three-carbon homologation of triorganozincates: Convergent three-component coupling of propargylic substrates, triorganozincates, and electrophilic reagents [J].

Harada, T ;

Katsuhira, T ;

Osada, A ;

Iwazaki, K ;

Maejima, K ;

Oku, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (46) :11377-11390

[7] STEREOSELECTIVE SYNTHESIS OF GEM-DISUBSTITUTED CYCLOPROPANES FROM GEM-DIBROMOCYCLOPROPANES [J].

HARADA, T ;

KATSUHIRA, T ;

HATTORI, K ;

OKU, A .

TETRAHEDRON LETTERS, 1989, 30 (44) :6039-6040

[8] GENERATION AND ALKYLATION REACTION OF LITHIUM 1-HALOCYCLOPROPYLZINCATE [J].

HARADA, T ;

HATTORI, K ;

KATSUHIRA, T ;

OKU, A .

TETRAHEDRON LETTERS, 1989, 30 (44) :6035-6038

[9] GENERATION AND ALKYLATION REACTION OF 1-BROMOALKENYLZINCATE [J].

HARADA, T ;

HARA, D ;

HATTORI, K ;

OKU, A .

TETRAHEDRON LETTERS, 1988, 29 (31) :3821-3824

[10] Trimagnesium-bridged trinuclear ferrocenophanes cocomplexed with solvated mononuclear alkali metal amide molecules [J].

Henderson, KW ;

Kennedy, AR ;

Mulvey, RE ;

O'Hara, CT ;

Rowlings, RB .

CHEMICAL COMMUNICATIONS, 2001, (17) :1678-1679

← 1 2 3 →