使用基于联芳基膦的催化剂体系实现芳基甲磺酸酯和对甲苯磺酸酯的施蒂勒交叉偶联反应。
STILLE CROSS-COUPLING REACTIONS OF ARYL MESYLATES AND TOSYLATES USING A BIARYLPHOSPHINE BASED CATALYST SYSTEM.
作者信息
Naber John R, Fors Brett P, Wu Xiaoxing, Gunn Jonathon, Buchwald Stephen L
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
出版信息
Heterocycles. 2010 Feb 26;80(2):1215-1226. doi: 10.3987/COM-09-S(S)105.
Abstract
A catalyst system for the Stille cross-coupling reactions of aryl mesylates and tosylates is reported. Using the combination of Pd(OAc), XPhos, and CsF in -BuOH an array of aryl and heteroaryl sulfonates were successfully employed in these reactions. Morever, heteroarylstannanes, such as furyl, thiophenyl, and -methylpyrrole, which are often prone to decomposition, were efficiently coupled under these conditions. -substitution on the stannane coupling partner was well tolerated; however, the presence of substituents on the aryl sulfonates greatly reduced the proficiency of these reactions.
摘要
报道了一种用于芳基甲磺酸酯和甲苯磺酸酯的Stille交叉偶联反应的催化剂体系。使用Pd(OAc)₂、XPhos和CsF在叔丁醇中的组合，一系列芳基和杂芳基磺酸盐成功地用于这些反应。此外，经常易于分解的杂芳基锡烷，如呋喃基、噻吩基和N-甲基吡咯，在这些条件下能有效偶联。锡烷偶联伙伴上的α-取代具有良好的耐受性；然而，芳基磺酸盐上存在β-取代基会大大降低这些反应的效率。
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