Synthesis and Enhanced Activity of Etherlized Ferrocenylphosphine for the Palladium-Catalyzed Suzuki Reaction

doi:10.3724/SP.J.1095.2011.00541

Chinese Journal of Applied Chemistry ›› 2011, Vol. 28 ›› Issue (08): 887-891.DOI: 10.3724/SP.J.1095.2011.00541

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Synthesis and Enhanced Activity of Etherlized Ferrocenylphosphine for the Palladium-Catalyzed Suzuki Reaction

YU Hongwei^2,3, GUAN Min², TONG Qingsong¹, JIA Li¹, JIN Zilin², SHI Jicheng^1*

(1.College of Chemistry and Materials Science,Fujian Key
Laboratory of Polymer Materials,Fujian Normal University,Fuzhou 350007;
2.State Key Laboratory of Fine Chemicals,Dalian University of Technology,Dalian;
3.School of Chemical Engineering,Shijiazhuang College,Shijiazhuang)

Received:2010-09-15 Revised:2010-10-27 Published:2011-08-10 Online:2011-08-10

Abstract

Abstract:

A new etherlized ferrocenylphosphine ligand, 2-diphenylphosphino-ferrocenyl-ethyl-5-hydroxyl-3-oxo-pentyl ether, was prepared by the reaction of acetyl 1-(diphenylphosphinoferrocenyl)ethyl ester with diethylene glycol in 77% yield. Its structure was characterized by 1H NMR, 13C NMR, 31P NMR and MS. The synthesized ferrocenylphosphine has been applied as supporting ligand in the palladium-catalyzed Suzuki reaction; its ligated palladium catalyst is effective for coupling a range of aryl bromides as well as aryl chlorides having electron-withdrawing groups with phenylboronic acid to prepare the corresponding biaryls. The possible coordination of ether-oxygen to the Pd center may enhance the catalytic performance of the ligand for cross-coupling reaction.

Key words: ferrocenylphosphine, etherlization, palladium, Suzuki reaction, biaryl

CLC Number:

O643.3

YU Hongwei2,3, GUAN Min2, TONG Qingsong1, JIA Li1, JIN Zilin2, SHI Jicheng1*. Synthesis and Enhanced Activity of Etherlized Ferrocenylphosphine for the Palladium-Catalyzed Suzuki Reaction[J]. Chinese Journal of Applied Chemistry, 2011, 28(08): 887-891.

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Synthesis and Enhanced Activity of Etherlized Ferrocenylphosphine for the Palladium-Catalyzed Suzuki Reaction

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