Secondary phosphine oxides: Versatile ligands in transition metal-catalyzed cross-coupling reactions

被引:178
作者
Shaikh, Tanveer Mahamadali [1 ]
Weng, Chia-Ming [1 ]
Hong, Fung-E [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 40227, Taiwan
关键词
Secondary phosphine oxide (SPO); Cross-coupling; SPO in asymmetric reactions; Density functional theory (DFT); Palladium; CARBON-CARBON BOND; CHIROGENIC DIAMINOPHOSPHINE OXIDES; ASYMMETRIC ALLYLIC AMINATION; PREPARING AROMATIC KETONES; ARYL GRIGNARD-REAGENTS; HIGHLY-ACTIVE CATALYST; SUZUKI-MIYAURA TYPE; ACYL CHLORIDES; ACID-CHLORIDES; ARYLBORONIC ACIDS;
D O I
10.1016/j.ccr.2011.11.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This review describes the development in the use of secondary phosphine oxides ligands in transition-metal-catalyzed oxidative coupling reactions to the formation of C-C, C-N and C-S bonds. Also the developments in the recent literature are highlighted in the areas of cycloaddition, coupling of acyl halide with organometallic reagents, oxidations and other reactions. The secondary phosphine oxides are known to exist in the tautomeric forms and are configurationally stable; this property enables a variety of useful transformations for accessing optically active organophosphorus compounds which are useful in the formation of C-C bonds and asymmetric hydrogenation reactions. Finally, the mechanistic aspect employing DFT technique in these oxidative coupling reactions is described in this article. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:771 / 803
页数:33
相关论文
共 50 条
[41]   Iron-Catalyzed Cross-Coupling Reactions Tuned by Bulky Ortho-Phenylene Bisphosphine Ligands [J].
Adak, Laksmikanta ;
Hatakeyama, Takuji ;
Nakamura, Masaharu .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2021, 94 (03) :1125-1141
[42]   Preparation and application of indolyl secondary phosphine oxides in palladium complexes catalyzed Suzuki-Miyaura cross-coupling reaction [J].
Chang, Yen-Yu ;
Hong, Fung-E .
TETRAHEDRON, 2013, 69 (10) :2327-2335
[43]   Formation of Transient Anionic Metal Clusters in Palladium/Diene-Catalyzed Cross-Coupling Reactions [J].
Kolter, Marlene ;
Koszinowski, Konrad .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (58) :13376-13384
[44]   Recent Progress in the Functionalization of Benzo-γ-Pyrones via Transition-Metal Catalyzed Cross-Coupling Reactions [J].
Ming, Xianjun ;
Yang, Kan ;
Gao, Biao ;
Gu, Qinlan ;
Wang, Jinxin .
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2016, 13 (01) :31-48
[45]   Modular Synthesis of Biaryl-Substituted Phosphine Ligands: Application in Microwave-Assisted Palladium-Catalyzed C-N Cross-Coupling Reactions [J].
Singh, Chandani ;
Rathod, Jayant ;
Jha, Vishwajeet ;
Panossian, Armen ;
Kumar, Pradeep ;
Leroux, Frederic R. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (29) :6515-6525
[46]   More than bystanders: The effect of Olefins on transition-metal-catalyzed cross-coupling reactions [J].
Johnson, Jeffrey B. ;
Rovis, Tomislav .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (05) :840-871
[47]   Usage of the Carboxylate Leaving Group in Transition-metal-catalyzed Cross-coupling and Related Reactions [J].
Kuwano, Ryoichi .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (11) :1263-1270
[48]   Recent Advances in Transition-Metal-Catalyzed Sonogashira Cross-Coupling Reactions of Alkyl Electrophiles [J].
Zhao, Xian ;
Liu, Wei .
SYNTHESIS-STUTTGART, 2024, 56 (08) :1244-1258
[49]   Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions [J].
Liu, Chao ;
Zhang, Hua ;
Shi, Wei ;
Lei, Aiwen .
CHEMICAL REVIEWS, 2011, 111 (03) :1780-1824
[50]   A Highly Efficient Cross-Coupling Mode via the Release of Small Molecules: Transition Metal-Catalyzed Unimolecular Fragment Coupling (UFC) [J].
Tian, Tian ;
Uei, Shuhei ;
Li, Zhiping ;
Nishihara, Yasushi .
CHEMCATCHEM, 2024, 16 (22)