一种新型三齿二茂铁基膦配体的催化效率：在10⁻¹至10⁻⁴mol%的低催化剂负载量下，炔烃与芳基溴化物和氯化物的Sonogashira交叉偶联反应

Catalytic efficiency of a new tridentate ferrocenyl phosphine auxiliary: Sonogashira cross-coupling reactions of alkynes with aryl bromides and chlorides at low catalyst loadings of 10(-1) to 10(-4) mol %.

作者信息

Hierso Jean-Cyrille, Fihri Aziz, Amardeil Régine, Meunier Philippe, Doucet Henri, Santelli Maurice, Ivanov Vladimir V

机构信息

Laboratoire de Synthèse et d'Electrosynthèse Organométalliques UMR-CNRS 5188, Université de Bourgogne, 9 Avenue Alain Savary, 21078 Dijon, France.

出版信息

Org Lett. 2004 Sep 30;6(20):3473-6. doi: 10.1021/ol048870z.

DOI:10.1021/ol048870z

PMID:15387526

Abstract

[structure: see text] The catalytic activity in Sonogashira cross-coupling reactions of alkynes with a variety of aryl halides (including chlorides) using a multidentate ferrocenyl phosphine is presented. The novel mixed ferrocenyl aryl/alkyl triphosphine is thermally stable and insensitive to air or moisture, and its robustness allows aryl alkynylation at 10(-1) to 10(-4) mol % catalyst loadings with TONs up to 250,000. Copper-free coupling using phenylacetylene is also accessible in good yield.

摘要

[结构：见正文] 本文介绍了使用多齿二茂铁基膦在炔烃与多种芳基卤化物（包括氯化物）的Sonogashira交叉偶联反应中的催化活性。新型混合二茂铁基芳基/烷基三膦热稳定，对空气或湿气不敏感，其稳定性使得在催化剂负载量为10⁻¹至10⁻⁴摩尔％的情况下进行芳基炔基化反应，TONs高达250,000。使用苯乙炔进行无铜偶联也能获得良好的产率。