Bromine-magnesium exchange of 5-bromo-2-picoline via an organomagnesium complex nBu2iPrMgLi:: a new preparation methodology of functionalized picolines under noncryogenic conditions

被引：14

作者：

Kii, S

Akao, A

Iida, T

Mase, T

Yasuda, N

机构：

[1] Banyu Pharmaceut Co Ltd, Proc Res, Okazaki, Aichi 4440858, Japan

[2] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 12期

关键词：

D O I：

10.1016/j.tetlet.2006.01.095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organomagnesium complex "(Bu2PrMgLi)-Pr-i, readily prepared from "BuLi and (PrMgCl)-Pr-i (2:1), is quite efficient for the bromine-magnesium exchange of 5-bromo-2-picoline under noncryogenic conditions (at -10 degrees C). The resulting picolylmagnesium complex reacts with various electrophiles to afford functionalized picolines. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1877 / 1879

页数：3

共 25 条

[1] Bromine-magnesium-exchange as a general tool for the preparation of polyfunctional aryl and heteroaryl magnesium-reagents
Abarbri, M
Dehmel, F
Knochel, P
[J]. TETRAHEDRON LETTERS, 1999, 40 (42) : 7449 - 7453
[2] Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange
Abarbri, M
Thibonnet, J
Bérillon, L
Dehmel, F
Rottländer, M
Knochel, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) : 4618 - 4634
[3] Bérillon L, 1998, SYNLETT, P1359
[4] 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
[5] Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines:: a convenient access to functionalized quinolines
Dumouchel, S
Mongin, F
Trécourt, F
Quéguiner, G
[J]. TETRAHEDRON LETTERS, 2003, 44 (10) : 2033 - 2035
[6] Synthesis and reactivity of lithium tri(quinolinyl)magnesates
Dumouchel, S
Mongin, F
Trécourt, F
Quéguiner, G
[J]. TETRAHEDRON, 2003, 59 (43) : 8629 - 8640
[7] Aggregative activation in heterocyclic chemistry.: Part 5.: Lithiation of pyridine and quinoline with the complex base BuLi•Me2N(CH2)2OLi (BuLi•LiDMAE)
Gros, P
Fort, Y
Caubère, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (24): : 3597 - 3600
[8] GROS P, 1995, TETRAHEDRON LETT, V36, P4791
[9] Aggregative activation in heterocyclic chemistry .4. Metallation of 2-methoxypyridine: unusual behaviour of the new unimetal superbase BuLi-Me2N(CH2)(2)OLi (BuLi-LiDMAE)
Gros, P
Fort, Y
Caubere, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (20): : 3071 - 3080
[10] A facile one-pot synthesis of alkyl aryl sulfides from aryl bromides
Ham, JY
Yang, IH
Kang, HJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) : 3236 - 3239

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