Palladium-catalysed alkynylations of 2-pyrone (pyran-2-one) halides

被引:32
|
作者
Fairlamb, IJS [1 ]
Lu, FJ [1 ]
Schmidt, JP [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源
SYNTHESIS-STUTTGART | 2003年 / 16期
关键词
palladium; Negishi reaction; Sonogashira reaction; 2-pyrones;
D O I
10.1055/s-2003-42405
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 2-pyrone sub-unit is found in a large number of natural products possessing broad-spectrum biological activity. As such, efficient synthetic methods are required to enable facile access to substituted 2-pyrone derivatives. Important conditions for the Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone (3a) have been developed, and compared against Negishi's methodology. The best conditions for Sonogashira alkynylation was found to be the use of Pd/C with added Ph3P as the catalyst, in the presence of catalytic Cut, in a mixture of MeCN and Et3N at reflux. Using Negishi's standard conditions, terminal alkynylzinc reagents, generated in situ from terminal alkynes with LDA or n-BuLi and subsequent reaction with anhydrous ZnBr2, were reacted with 3a at room temperature using Pd(PPh3)(4) as the catalyst in THF.
引用
收藏
页码:2564 / 2570
页数:7
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