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

页码：2564 / 2570

页数：7

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