Nickel-Catalyzed C-H Alkylations: Direct Secondary Alkylations and Trifluoroethylations of Arenes

被引:239
作者
Song, Weifeng [1 ]
Lackner, Sebastian [1 ]
Ackermann, Lutz [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
基金
欧洲研究理事会;
关键词
auxiliary assistance; C-H activation; nickel; secondary alkylation; trifluoroethylation; UNACTIVATED C(SP(3))-H BONDS; ELECTRON-DEFICIENT ARENES; CROSS-COUPLING REACTIONS; ALKYL-HALIDES; AROMATIC AMIDES; ACID DERIVATIVES; ACTIVATION; FUNCTIONALIZATION; ARYLATION; HYDROHETEROARYLATION;
D O I
10.1002/anie.201309584
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A versatile nickel catalyst allowed for C-H alkylations of unactivated arenes with challenging secondary alkyl bromides and chlorides. The high catalytic efficacy also set the stage for direct secondary alkylations of indoles as well as C-H trifluoroethylations with ample substrate scope.
引用
收藏
页码:2477 / 2480
页数:4
相关论文
共 50 条
[21]   Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes [J].
Li, Ze-Lin ;
Wu, Peng-Yu ;
Cai, Chun .
NEW JOURNAL OF CHEMISTRY, 2019, 43 (08) :3462-3468
[22]   Nickel-catalyzed C-H bond Alkoxylation of Amides with Alcohols [J].
Rajesh, Nimmakuri ;
Sundararaju, Basker .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) :1368-1371
[23]   Nickel-Catalyzed Stereospecific C-H Coupling of Benzamides with Epoxides [J].
Xu, Shibo ;
Takamatsu, Kazutaka ;
Hirano, Koji ;
Miura, Masahiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (36) :11797-11801
[24]   A General Strategy for the Nickel-Catalyzed C-H Alkylation of Anilines [J].
Ruan, Zhixiong ;
Lackner, Sebastian ;
Ackermann, Lutz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (09) :3153-3157
[25]   Nickel-catalyzed intramolecular C-H arylation using aryl pivalates as electrophiles [J].
Wang, Jiayi ;
Ferguson, Devin M. ;
Kalyani, Dipannita .
TETRAHEDRON, 2013, 69 (27-28) :5780-5790
[26]   Electrocatalytic Formal C(sp2)-H Alkylations via Nickel-Catalyzed Cross-Electrophile Coupling with Versatile Arylsulfonium Salts [J].
Michiyuki, Takuya ;
Homoelle, Simon L. ;
Pandit, Neeraj K. ;
Ackermann, Lutz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (29)
[27]   Nickel-Catalyzed Benzylation of C-H Bonds in Aromatic Amides with Benzyltrimethylammonium Halides [J].
Sasagawa, Akane ;
Yamaguchi, Mao ;
Ano, Yusuke ;
Chatani, Naoto .
ISRAEL JOURNAL OF CHEMISTRY, 2017, 57 (10-11) :964-967
[28]   Nickel-Catalyzed C-H Silylation of Arenes with Vinylsilanes: Rapid and Reversible β-Si Elimination [J].
Elsby, Matthew R. ;
Johnson, Samuel A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (27) :9401-9407
[29]   Palladium-Catalyzed Enantioselective Allylic Alkylations through C-H Activation [J].
Trost, Barry M. ;
Thaisrivongs, David A. ;
Donckele, Etienne J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1523-1526
[30]   Palladium-catalyzed Direct C-H Bond Arylation of Simple Arenes with Aryltrimethylsilanes [J].
Funaki, Kenji ;
Kawai, Hiroshi ;
Sato, Tetsuo ;
Oi, Shuichi .
CHEMISTRY LETTERS, 2011, 40 (09) :1050-1052