Ammonia free partial reduction of aromatic compounds using lithium di-tert-butylbiphenyl (LiDBB)

被引：72

作者：

Donohoe, TJ ^{[1
]}

House, D ^{[1
]}

机构：

[1] Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 14期

关键词：

D O I：

10.1021/jo0257593

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of a series of hetero- and carbocyclic aromatic compounds under ammonia free conditions is described. By using LiDBB as a source of electrons, bis(methoxyethyl)amine (BMEA) as a protonating agent, and THF as a solvent, we were able to accomplish reductions more usually performed under Birch type conditions. Moreover, the use of these conditions was further enhanced by the tolerance of the reducing system toward reactive electrophiles that cannot be used successfully in ammonia.

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页码：5015 / 5018

页数：4

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共 19 条

[1] PI GROUPS IN ION-PAIR BONDING - STABILIZATION OF DIANION OF NAPHTHALENE BY LITHIUM TETRAMETHYLETHYLENEDIAMINE [J].

BROOKS, JJ ;

RHINE, W ;

STUCKY, GD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (21) :7346-&

[2] Use of aromatic radical-anions in the absence of THF.: Tandem formation and cyclization of benzyllithiums derived from the attack of homo- and bishomoallyllithiums on α-methylstyrenes:: Two-pot synthesis of cuparene [J].

Cohen, T ;

Kreethadumrongdat, T ;

Liu, XJ ;

Kulkarni, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3478-3483

[3] ELECTRON SPIN RESONANCE SPECTRA OF SOME GROUP 4-B SUBSTITUTED BIPHENYL ANION RADICALS . DATIVE PI-BONDING [J].

CURTIS, MD ;

ALLRED, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (12) :2554-&

[4] Stereoselective reduction of chiral 2-furoic acid derivatives using group I metals in ammonia [J].

Donohoe, TJ ;

Calabrese, AA ;

Stevenson, CA ;

Ladduwahetty, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (22) :3724-3731

[5] Reduction of electron-deficient pyrroles using group I and II metals in ammonia [J].

Donohoe, TJ ;

Guyo, PM ;

Beddoes, RL ;

Helliwell, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (04) :667-676

[6] Birch reduction of electron-deficient pyrroles [J].

Donohoe, TJ ;

Guyo, PM .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7664-7665

[7] Stereoselective reductive alkylation of 2,5-disubstituted pyrroles: a role for naphthalene in the partial reduction of heterocycles [J].

Donohoe, TJ ;

Harji, RR ;

Cousins, RPC .

TETRAHEDRON LETTERS, 2000, 41 (09) :1327-1330

[8] The partial reduction of heterocycles: an alternative to the Birch reduction [J].

Donohoe, TJ ;

Harji, RR ;

Cousins, RPC .

TETRAHEDRON LETTERS, 2000, 41 (09) :1331-1334

[9] Stereoselectivity in the birch reduction of 2-furoic acid derivatives [J].

Donohoe, TJ ;

Helliwell, M ;

Stevenson, CA ;

Ladduwahetty, T .

TETRAHEDRON LETTERS, 1998, 39 (19) :3071-3074

[10] Reductive aldol reactions on aromatic heterocycles [J].

Donohoe, TJ ;

Ace, KW ;

Guyo, PM ;

Helliwell, M ;

McKenna, J .

TETRAHEDRON LETTERS, 2000, 41 (07) :989-993