Ni-Catalyzed Asymmetric C-P Cross-Coupling Reaction for the Synthesis of Chiral Heterocyclic Phosphine Oxides

被引:14
作者
Cui, Ranran [1 ]
Wang, Yinqi [1 ]
Yuwen, Liyan [1 ]
Gao, Li [1 ]
Huang, Zhuo [1 ]
Wang, Wei-Han [1 ]
Zhang, Qing-Wei [1 ]
机构
[1] Univ Sci & Technol China, Key Lab Precis & Intelligent Chem, Dept Chem, Hefei 230026, Peoples R China
关键词
MECHANISTIC IMPLICATIONS; NICKEL CATALYSIS; CARBON; PHOSPHORYLATION; DERIVATIVES; ARYLATION; LIGHT;
D O I
10.1021/acs.orglett.3c02216
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nickelperforms excellently in C-C and C-X cross-couplingreactions. Here, we disclose a Ni(II)-catalyzed asymmetric C-Pcross-coupling reaction to afford valuable chiral heterocyclic tertiaryphosphine oxides. The method is mild and efficient, which invokesa self-sustained nickel catalytic cycle without an external reductant,light irradiation, or electricity.
引用
收藏
页码:6139 / 6142
页数:4
相关论文
共 43 条
[1]   Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines [J].
Beaud, Rodolphe ;
Phipps, Robert J. ;
Gaunt, Matthew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (40) :13183-13186
[2]  
Cui R., 2023, CHEMRXIV, DOI [10.26434/chemrxiv-2023-p8qvx, DOI 10.26434/CHEMRXIV-2023-P8QVX]
[3]   P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides [J].
Dai, Qiang ;
Li, Wenbo ;
Lo, Zhiming ;
Zhang, Junliang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (51) :20556-20564
[4]   Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization [J].
Diccianni, Justin ;
Lin, Qiao ;
Diao, Tianning .
ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (04) :906-919
[5]   Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates [J].
Fu, Wai Chung ;
So, Chau Ming ;
Kwong, Fuk Yee .
ORGANIC LETTERS, 2015, 17 (23) :5906-5909
[6]   Overcoming limitations in dual photoredox/nickel-catalysed C-N cross-couplings due to catalyst deactivation [J].
Gisbertz, Sebastian ;
Reischauer, Susanne ;
Pieber, Bartholomaeus .
NATURE CATALYSIS, 2020, 3 (08) :611-620
[7]   Molecular Metal Phosphonates [J].
Goura, Joydeb ;
Chandrasekhar, Vadapalli .
CHEMICAL REVIEWS, 2015, 115 (14) :6854-6965
[8]   Photoredox sheds new light on nickel catalysis: from carbon-carbon to carbon-heteroatom bond formation [J].
Gui, Yong-Yuan ;
Sun, Liang ;
Lu, Zhi-Peng ;
Yu, Da-Gang .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (04) :522-526
[9]   Phosphine Organocatalysis [J].
Guo, Hongchao ;
Fan, Yi Chiao ;
Sun, Zhanhu ;
Wu, Yang ;
Kwon, Ohyun .
CHEMICAL REVIEWS, 2018, 118 (20) :10049-10293
[10]   A dual catalytic strategy for carbon-phosphorus cross-coupling via gold and photoredox catalysis [J].
He, Ying ;
Wu, Hongmiao ;
Toste, F. Dean .
CHEMICAL SCIENCE, 2015, 6 (02) :1194-1198