Bromine-magnesium-exchange as a general tool for the preparation of polyfunctional aryl and heteroaryl magnesium-reagents

被引：102

作者：

Abarbri, M ^{[1
]}

Dehmel, F ^{[1
]}

Knochel, P ^{[1
]}

机构：

[1] Univ Munich, Inst Organ Chem, D-81377 Munich, Germany

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(99)01404-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope of the Br-Mg-exchange reaction for the preparation of polyfunctional aryl and heteroaryl magnesium reagents has been studied. Various functional groups (ester, cyano, bromide) were tolerated in the exchange reaction allowing the preparation of polyfunctional Mg-reagents. Several dibromo- or tribromoheterocycles undergo a chemoselective mono-Br-Mg exchange leading to highly functionalized heterocycles. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7449 / 7453

页数：5

共 22 条

[1] Bérillon L, 1998, SYNLETT, P1359
[2] Magnesium promoted cyclopropanation reactions of allylic alcohols
Bolm, C
Pupowicz, D
[J]. TETRAHEDRON LETTERS, 1997, 38 (42) : 7349 - 7352
[3] Boymond L, 1998, ANGEW CHEM INT EDIT, V37, P1701, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1701::AID-ANIE1701>3.0.CO
[4] 2-U
[5] MANGANESE(II) CATALYSIS .2. REACTION OF VINYL AND ARYL HALIDES BY ORGANOMAGNESIUM COMPOUNDS IN PRESENCE OF MANGANESE(II)
CAHIEZ, G
BERNARD, D
NORMANT, JF
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 113 (02) : 107 - 113
[6] A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010
Cai, DW
Hughes, DL
Verhoeven, TR
[J]. TETRAHEDRON LETTERS, 1996, 37 (15) : 2537 - 2540
[7] PREPARATION OF PYRIDYL GRIGNARD-REAGENTS AND CROSS COUPLING REACTIONS WITH SULFOXIDES BEARING AZAHETEROCYCLES
FURUKAWA, N
SHIBUTANI, T
FUJIHARA, H
[J]. TETRAHEDRON LETTERS, 1987, 28 (47) : 5845 - 5848
[8] Use of the vinyl group as an efficient protecting group for azole N-atoms: Synthesis of polyfunctionalized imidazoles and thieno[2,3-d]reversible arrow[3,2-d]imidazole
Hartley, DJ
Iddon, B
[J]. TETRAHEDRON LETTERS, 1997, 38 (26) : 4647 - 4650
[9] Organozinc mediated reactions
Knochel, P
Perea, JJA
Jones, P
[J]. TETRAHEDRON, 1998, 54 (29) : 8275 - 8319
[10] SINGLE-FLASK POLYFUNCTIONALIZATION OF THE IMIDAZOLE RING - A STREAMLINED ROUTE TO THE ANTITUMOR AGENT CARMETHIZOLE
LIPSHUTZ, BH
HAGEN, W
[J]. TETRAHEDRON LETTERS, 1992, 33 (40) : 5865 - 5868

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