Di-t-butyl(ferrocenylmethyl)phosphine:: air-stability, structural characterization, coordination chemistry, and application to palladium-catalyzed cross-coupling reactions

被引：17

作者：

Sliger, MD ^{[1
]}

Broker, GA ^{[1
]}

Griffin, ST ^{[1
]}

Rogers, RD ^{[1
]}

Shaughnessy, KH ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2005年 / 690卷 / 06期

基金：

美国国家科学基金会;

关键词：

phosphine; ferrocene; palladium; cross-coupling; Suzuki coupling; heck coupling;

D O I：

10.1016/j.jorganchem.2004.12.022

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Di-t-butyl(ferrocenylmethyl)phosphine (1) has been isolated and structurally characterized. This ligand was found to be reasonably air stable as a solid and it has been shown to possess electron donating ability similar to that of tri-i-propylphosphine. A palladium catalyst bearing this ligand performed room temperature Suzuki-Miyaura coupling reactions with aryl bromides. Modest Heck coupling reactivity with aryl bromides was also observed at 100 degrees C. Complexation of 1 with Pd-2(dba)(3) led to formation of (1)(2)Pd-0. Addition of 4-bromoanisole to solutions containing both 1 and Pd-2(dba)(3) led to formation of an oxidative addition product when 1:Pd ratios were <= 1. With a 2:1 ratio of 1:Pd, monophosphine complex formation and oxidative addition were significantly inhibited. (c) 2004 Elsevier B.V. All rights reserved.

引用

页码：1478 / 1486

页数：9

共 61 条

[1] Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones [J].