Macromolecular effect: Synthesis of a ferrocenylmethylphosphine-containing polymer as highly efficient ligands for room-temperature palladium(0)-catalyzed Suzuki cross-coupling reactions of aryl chlorides

被引:104
作者
Hu, QS [1 ]
Lu, Y
Tang, ZY
Yu, HB
机构
[1] CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
[2] CUNY, Grad Ctr, Staten Isl, NY 10314 USA
关键词
D O I
10.1021/ja029021e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The design and synthesis of a ferrocenylmethylphosphine-containing polymer and its application as efficient ligands for the room-temperature Pd(0)-catalyzed cross-coupling reaction of aryl chlorides with arylboronic acids, for which corresponding monomeric monophosphines are totally inactive, are described. Our work demonstrated that rather small monophosphine moieties such as RPPh2 can be used as highly efficient ligands when appropriately incorporated into a rigid and sterically regular polymer network and using monophosphine-containing polymers as ligands is a feasible approach to access highly active (monophosphine)-palladium(0) complexes. The macromolecular approach described here may open a new avenue to other coordinatively unsaturated (monoligand)-transition metal complexes which are potentially useful in organic synthesis. Copyright © 2003 American Chemical Society.
引用
收藏
页码:2856 / 2857
页数:2
相关论文
共 50 条
[42]   Synthesis and palladium(II) metal chemistry of thiazoline/imidazoline derived ligands: An efficient catalyst for cross-coupling reactions of arylboronic acids with acid chlorides and aryl halides [J].
Sudharsan, Murugesan ;
Suresh, D. .
INORGANICA CHIMICA ACTA, 2018, 483 :598-608
[43]   Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides [J].
Chen, Bing-Zhi ;
Zhi, Man-Ling ;
Wang, Chuang-Xin ;
Chu, Xue-Qiang ;
Shen, Zhi-Liang ;
Loh, Teck-Peng .
ORGANIC LETTERS, 2018, 20 (07) :1902-1905
[44]   Highly efficient palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl bromides using 2-(diphenylphosphino) benzaldoxime ligand [J].
Xu, L ;
Zhu, D ;
Wu, F ;
Wang, RL ;
Wan, BS .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 237 (1-2) :210-214
[45]   Design and synthesis of thioether-imidazolium chlorides as efficient ligands for palladium-catalyzed Suzuki-Miyaura coupling of aryl bromides with arylboronic acids [J].
Kuriyama, Masami ;
Shimazawa, Rumiko ;
Shirai, Ryuichi .
TETRAHEDRON, 2007, 63 (38) :9393-9400
[46]   Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids [J].
Jin, Zhong ;
Guo, Su-Xian ;
Gu, Xiao-Peng ;
Qiu, Ling-Ling ;
Song, Hai-Bing ;
Fang, Jian-Xin .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (10) :1575-1585
[47]   An atom-efficient palladium-catalyzed cross-coupling reaction of triarylbismuths with acid chlorides: synthesis of diaryl and alkyl aryl ketones [J].
Rao, Maddah L. N. ;
Venkatesh, Varadhachari ;
Jadhav, Deepak N. .
TETRAHEDRON LETTERS, 2006, 47 (39) :6975-6978
[48]   The Highly Efficient Suzuki-Miyaura Cross-Coupling of (Hetero)aryl Chlorides and (Hetero)arylboronic Acids Catalyzed by "Bulky-yet-Flexible" Palladium-PEPPSI Complexes in Air [J].
Ouyang, Jia-Sheng ;
Li, Yan-Fang ;
Huang, Fei-Dong ;
Lu, Dong-Dong ;
Liu, Feng-Shou .
CHEMCATCHEM, 2018, 10 (02) :371-375
[49]   Synthesis of novel bisphosphine-containing polymers and their applications as bidentate ligands for nickel(0)-catalyzed cross-coupling reactions [J].
Lu, Yong ;
Plocher, Elizabeth ;
Hu, Qiao-Sheng .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) :841-845
[50]   An efficient water-soluble surfactant-type palladium catalyst for Suzuki cross-coupling reactions in pure water at room temperature [J].
Qiu, Pei ;
Zhao, Jing Yang ;
Shi, Xu ;
Duan, Xin Hong .
NEW JOURNAL OF CHEMISTRY, 2016, 40 (08) :6568-6572