通过 Pd-PEPPSI-IPent 实现高效低温 Stille-Migita 交叉偶联反应合成杂芳族化合物。

An efficient low-temperature Stille-Migita cross-coupling reaction for heteroaromatic compounds by Pd-PEPPSI-IPent.

机构信息

Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada.

出版信息

Chemistry. 2010 Apr 12;16(14):4279-83. doi: 10.1002/chem.200903337.

DOI:10.1002/chem.200903337

PMID:20209529

Abstract

The reactivity of Pd-PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization, and Initiation) precatalysts in the Stille-Migita cross-coupling reaction between heteroaryl stannanes and aryl or heteroaryl halides was evaluated. In general, Pd-PEPPSI-IPent (IPent=diisopentylphenylimidazolium derivative) demonstrated high efficiency over a variety of challenging aryl or heteroaryl halides with thiophene-, furan-, pyrrole-, and thiazole-based organostannanes when compared with Pd-PEPPSI-IPr (IPr=diisopropylphenylimidazolium derivative). The transformations proceeded at appreciably lower temperatures (30-80 degrees C) than triarylphosphine-based Pd catalysts, improving the scope of this useful carbon-carbon bond-forming process.

摘要

评价了 Pd-PEPPSI（吡啶，增强，前催化剂，制备，稳定和引发）前催化剂在芳基或杂芳基卤化物与杂芳基锡烷之间的 Stille-Migita 交叉偶联反应中的反应性。一般来说，与 Pd-PEPPSI-IPr（IPr=二异丙基苯基咪唑𬭩衍生物）相比，Pd-PEPPSI-IPent（IPent=二异戊基苯基咪唑𬭩衍生物）在各种具有挑战性的芳基或杂芳基卤化物与基于噻吩、呋喃、吡咯和噻唑的有机锡烷的反应中表现出高效率。这些转化在明显更低的温度（30-80 摄氏度）下进行，优于基于三芳基膦的 Pd 催化剂，从而扩大了这一有用的碳-碳键形成过程的范围。