钯催化的二氢吡喃基铟试剂与芳基卤化物之间的交叉偶联反应。C-芳基缩水甘油醛的合成。

Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. synthesis of C-aryl glycals.

作者信息

Lehmann Ute, Awasthi Smita, Minehan Thomas

机构信息

Department of Chemistry, Harvey Mudd College, Claremont, California 91711, USA.

出版信息

Org Lett. 2003 Jul 10;5(14):2405-8. doi: 10.1021/ol0345428.

DOI:10.1021/ol0345428

PMID:12841741

Abstract

[reaction: see text] Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reagents in the presence of 1-5 mol % Cl(2)Pd(PPh(3))(2) to produce substituted dihydropyrans 3 with minimal (<10%) dimer (4) formation. Organoindium reagents derived from D-glucal also undergo cross couplings with aryl iodides to produce C-aryl glycals.

摘要

[反应：见正文] 研究了三（二氢吡喃基）铟1与芳基卤化物2之间的钯（0）催化交叉偶联反应。在1-5 mol%的二氯双（三苯基膦）钯（Cl₂Pd(PPh₃)₂）存在下，芳基碘化物和缺电子芳基溴化物能与原位生成的铟试剂高效偶联，生成取代二氢吡喃3，二聚体（4）的生成量极少（<10%）。源自D-葡糖烯的有机铟试剂也能与芳基碘化物发生交叉偶联反应，生成C-芳基葡糖烯。