Combinatorial Nickel-Catalyzed Monofluoroalkylation of Aryl Boronic Acids with Unactivated Fluoroalkyl Iodides

被引:51
|
作者
Sheng, Jie
Ni, Hui-Qi
Liu, Ge
Li, Yan
Wang, Xi-Sheng [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China
基金
美国国家科学基金会;
关键词
CROSS-COUPLING REACTIONS; CARBON BOND FORMATION; ARYLBORONIC ACIDS; (2-PYRIDYL)SULFONYL GROUP; BENZYLIC FLUORINATION; ASYMMETRIC CATALYSIS; FLUOROMETHYL IODIDE; MEDICINAL CHEMISTRY; EMISSION-TOMOGRAPHY; EFFICIENT SYNTHESIS;
D O I
10.1021/acs.orglett.7b02012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A combinatorial nickel-catalyzed cross-coupling between arylboronic acids and unactived 1-fluoro-1-iodoalkanes has been developed, which demonstrated high efficiency, mild conditions, and excellent functional-group compatibility. Readily available nitrogen and phosphine ligands were combined with a nitrogen source, which in situ generated a variety of easily tunable catalysts to promote the fluoroalkylation for broad scopes of both coupling partners. This new strategy on combinatorial catalysis offers new solutions for nickel-catalyzed cross-coupling reactions.
引用
收藏
页码:4480 / 4483
页数:4
相关论文
共 50 条
  • [41] Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2
    Sun, Guo-Quan
    Zhang, Wei
    Liao, Li-Li
    Li, Li
    Nie, Zi-Hao
    Wu, Jin-Gui
    Zhang, Zhen
    Yu, Da-Gang
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [42] Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2
    Guo-Quan Sun
    Wei Zhang
    Li-Li Liao
    Li Li
    Zi-Hao Nie
    Jin-Gui Wu
    Zhen Zhang
    Da-Gang Yu
    Nature Communications, 12
  • [43] Nickel-catalyzed direct C-H arylation of unactivated arenes with aryl halides
    Xie, Guanlei
    Li, Tingyi
    Qu, Xiaoming
    Mao, Jincheng
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 340 (1-2) : 48 - 52
  • [44] Nickel-catalyzed olefination of unactivated aliphatic dithioacetals
    Huang, LF
    Huang, CH
    Stulgies, B
    de Meijere, A
    Luh, TY
    ORGANIC LETTERS, 2003, 5 (23) : 4489 - 4491
  • [45] Nickel-Catalyzed C-S Bond Formation: Synthesis of Aryl Sulfides from Arylsulfonyl Hydrazides and Boronic Acids
    Singh, Rahul
    Allam, Bharat Kumar
    Singh, Neetu
    Kumari, Kumkum
    Singh, Satish Kumar
    Singh, Krishna Nand
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1181 - 1186
  • [46] Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes
    Logan, Kaitlyn M.
    Sardini, Stephen R.
    White, Sean D.
    Brown, M. Kevin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) : 159 - 162
  • [47] Nickel-Catalyzed Carbon-Sulfur Bond Formation through Couplings of Aryl Iodides and Aryl Ethanethioates
    Mao, Pu
    Sui, Hong-Da
    Yuan, Jin-Wei
    Xiao, Yong-Mei
    Yang, Liang-Ru
    Mai, Wen-Peng
    CHEMISTRYSELECT, 2020, 5 (32): : 9908 - 9910
  • [48] Nickel-Catalyzed Intermolecular Insertion of Aryl Iodides to Nitriles: A Novel Method to Synthesize Arylketones
    Hsieh, Jen-Chieh
    Chen, Yen-Chung
    Cheng, An-Yi
    Tseng, Hsiao-Chun
    ORGANIC LETTERS, 2012, 14 (05) : 1282 - 1285
  • [49] Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides
    Wang, Wei
    Yao, Ken
    Wu, Fan
    SYNLETT, 2022, 33 (04) : 361 - 366
  • [50] Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides
    Arendt, Kevin M.
    Doyle, Abigail G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) : 9876 - 9880