Suzuki coupling of oxazoles

被引：77

作者：

Flegeau, Emmanuel Ferrer

Popkin, Matthew E.

Greaney, Michael F.

机构：

[1] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

[2] GlaxoSmithKline, Chem Dev, Tonbridge TN11 9AN, Kent, England

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 12期

关键词：

D O I：

10.1021/ol060591j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A protocol for the functionalization of the oxazole 2- and 4-positions using the Suzuki coupling reaction is described. 2-Aryl-4-trifloyloxazoles undergo rapid, microwave-assisted coupling with a range of aryl and heteroaryl boronic acids in good to excellent yields. The methodology is similarly effective using 4-aryl-2-chlorooxazoles as the coupling partner and has been extended to the synthesis of a novel class of homo-and heterodimeric 4,4-linked dioxazoles.

引用

页码：2495 / 2498

页数：4

共 34 条

[1] Application of palladium(0)-catalyzed processes to the synthesis of oxazole-containing partial ergot alkaloids
Anderson, BA
Becke, LM
Booher, RN
Flaugh, ME
Harn, NK
Kress, TJ
Varie, DL
Wepsiec, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) : 8634 - 8639
[2] Anderson BA, 1996, SYNTHESIS-STUTTGART, P583
[3] AOYAGI Y, 1992, HETEROCYCLES, V33, P257
[4] Synthesis and reaction of the first oxazol-4-ylboronates: Useful reagents for the preparation of the oxazole-containing biaryl compounds
Araki, H
Katoh, T
Inoue, M
[J]. SYNLETT, 2006, (04) : 555 - 558
[5] A two-stage iterative process for the synthesis of poly-oxazoles
Atkins, JM
Vedejs, E
[J]. ORGANIC LETTERS, 2005, 7 (15) : 3351 - 3354
[6] BARRETT AGM, 1995, SYNLETT, P415
[7] A synthetic approach towards the aromatic macrocyclic core of diazonamide A based on sp2-sp2 coupling protocols
Boto, A
Ling, M
Meek, G
Pattenden, G
[J]. TETRAHEDRON LETTERS, 1998, 39 (44) : 8167 - 8170
[8] Buzon RA, 2004, PCT Int. Appl., Patent No. [2,004,020,438, 2004020438]
[9] Synthesis of the C1′-C11′ oxazole-containing side chain of leucascandrolide A.: Application of a sonogashira cross-coupling
Dakin, LA
Langille, NF
Panek, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19) : 6812 - 6815
[10] DONDONI A, 1987, SYNTHESIS-STUTTGART, P693

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