Ferrocenyl phosphine-oxazaphospholidine oxide ligands for the Suzuki-Miyaura coupling of hindered aryl bromides and chlorides

被引：17

作者：

Vinci, Daniele ^{[1
]}

Martins, Nelson ^{[1
,2
]}

Saidi, Ourida ^{[1
]}

Bacsa, John ^{[1
]}

Brigas, Amadeu ^{[2
]}

Xiao, Jianliang ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

[2] Univ Algarve, Fac Ciencias & Tecnol, C CIQA, P-8005139 Faro, Portugal

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2009年 / 87卷 / 01期

关键词：

Suzuki-Miyaura coupling; ferrocenyl phosphines; aryl bromides; aryl chlorides; palladium; CHIRAL NATURAL-PRODUCTS; HIGHLY-ACTIVE CATALYST; ORGANOBORON COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; MONOPHOSPHINE LIGANDS; ASYMMETRIC-SYNTHESIS; SYNTHETIC REACTIONS; BIARYL COMPOUNDS; ORGANIC HALIDES; VANCOMYCIN;

D O I：

10.1139/V08-113

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of ferrocenyl oxazaphospholidine phosphines that differ electronically and sterically were investigated as ligands for the Suzuki-Miyaura cross-coupling reactions. One of these compounds, 1, was shown to be highly effective in the coupling reactions of bulky aryl bromides with boronic acids when combined with Pd(OAc)(2), while another, 2, was capable of coupling aryl chlorides with boronic acids. However, these ligands were less effective in asymmetric induction.

引用

页码：171 / 175

页数：5

共 47 条

[1] Recent applications of chiral ferrocene ligands in asymmetric catalysis [J].

Arrayas, Ramon Gomez ;

Adrio, Javier ;

Carretero, Juan Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7674-7715

[2] Ferrocenyl monophosphine ligands: Synthesis and applications in the Suzuki-Miyaura coupling of aryl chlorides [J].

Baillie, C ;

Zhang, LX ;

Xiao, JL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) :7779-7782

[3]

Barbour L.J., 2001, J SUPRAMOL CHEM, V1, P189, DOI [DOI 10.1016/S1472-7862(02)00030-8, 10.1016/S1472-7862(02)00030-8]

[4] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[5] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[6] Stereoselective total synthesis of axially chiral natural products via biaryl lactones [J].

Bringmann, G ;

Menche, D .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) :615-624

[7] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents [J].

Bringmann, G ;

Breuning, M ;

Tasler, S .

SYNTHESIS-STUTTGART, 1999, (04) :525-558

[8] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].

BRINGMANN, G ;

WALTER, R ;

WEIRICH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991

[9]

*BRUK AXS INC, 2007, SADABS VERS 2007 2 C

[10]

*BRUK AXS INC, 2005, SAINT PLUS VERS 6 45

← 1 2 3 4 5 →