Efficient copper(I)-catalyzed coupling of secondary phosphine oxides with aryl halides

被引:51
作者
Stankevic, Marek [1 ]
Wlodarczyk, Adam [1 ]
机构
[1] Marie Curie Sklodowska Univ, Fac Chem, Dept Organ Chem, PL-20614 Lublin, Poland
关键词
Coupling reaction; Copper(I) iodide; Secondary phosphine oxides; Tertiary phosphine oxides; Diphosphine dioxides; P BOND CONSTRUCTION; ASYMMETRIC HYDROGENATION; TERTIARY PHOSPHINES; CATALYZED FORMATION; OXAZOLINE LIGANDS; PHOSPHORUS; RESOLUTION; VERSATILE; BINAP; TRIARYLPHOSPHINES;
D O I
10.1016/j.tet.2012.10.064
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A catalytic system has been developed for the efficient synthesis of tertiary arylphosphine oxides by coupling of readily available secondary phosphine oxides with aryl bromides or iodides in the presence of copper(I) iodide as a catalyst and (S)-alpha-phenylethylamine as a ligand. The system exhibits high activity in the coupling of secondary diaryl-, alkylaryl- and dialkylphosphine oxides. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:73 / 81
页数:9
相关论文
共 50 条
[31]   Synthesis of Diarylalkynes by Iron/Copper Co-Catalyzed Decarboxylative sp-sp2 Coupling of Alkynyl Carboxylic Acids and Aryl Halides [J].
Li, Tingyi ;
Qu, Xiaoming ;
Zhu, Yan ;
Sun, Peng ;
Yang, Hailong ;
Shan, Yuqin ;
Zhang, Hongxin ;
Liu, Defu ;
Zhang, Xiang ;
Mao, Jincheng .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) :2731-2738
[32]   Copper(I)-Catalyzed Asymmetric Alkylation of Unsymmetrical Secondary Phosphines [J].
Zhang, Shuai ;
Xiao, Jun-Zhao ;
Li, Yan-Bo ;
Shi, Chang-Yun ;
Yin, Liang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (26) :9912-9921
[33]   Synthesis of P-Chiral Tertiary Phosphine Oxides by Copper-Catalyzed Dynamic Kinetic Asymmetric C-P Cross-Coupling [J].
Kang, Jie ;
Ren, Simu ;
Su, Bo .
SYNLETT, 2024, 35 (07) :741-746
[34]   Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings [J].
Zhai, Yuntong ;
Chen, Xiaofei ;
Zhou, Wei ;
Fan, Mengyang ;
Lai, Yisheng ;
Ma, Dawei .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (09) :4964-4969
[35]   Acceleration of CuI-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents using lithium chloride [J].
Nakata, Kenya ;
Feng, Chao ;
Tojo, Toshifumi ;
Kobayashi, Yuichi .
TETRAHEDRON LETTERS, 2014, 55 (42) :5774-5777
[36]   Efficient Copper-Catalyzed N-Arylation of Amides and Imidazoles with Aryl Iodides [J].
Ali, Md. Ashif ;
Saha, Prasenjit ;
Punniyamurthy, Tharmalingam .
SYNTHESIS-STUTTGART, 2010, (06) :908-910
[37]   A Simple and Efficient Ligand-Free Copper-Catalyzed C-N Bond Formation of Aryl (Hetero) Halides and N-Heteroaryl Amines [J].
Kommuri, Venkata Chandrasekhar ;
Tadiparthi, Krishnaji ;
Pawar, Lokesh ;
Arunachalampillai, Athimoolam .
POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (01) :665-673
[38]   Synthesis of Water-Soluble Phosphine Oxides by Pd/C-Catalyzed P-C Coupling in Water [J].
Rummelt, Stephan M. ;
Ranocchiari, Marco ;
van Bokhoven, Jeroen A. .
ORGANIC LETTERS, 2012, 14 (08) :2188-2190
[39]   [NiCl2(dppp)]-Catalyzed Cross-Coupling of Aryl Halides with Dialkyl Phosphite, Diphenylphosphine Oxide, and Diphenylphosphine [J].
Zhao, Yu-Long ;
Wu, Guo-Jie ;
Li, You ;
Gao, Lian-Xun ;
Han, Fu-She .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9622-9627
[40]   An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides [J].
Liu, Teng ;
Zhang, Yanqiong ;
Yu, Rong ;
Liu, Jianjun ;
Cheng, Feixiang .
SYNTHESIS-STUTTGART, 2020, 52 (02) :253-262