Asymmetric nickel-catalyzed negishi cross-couplings of secondary α-bromo amides with organozinc reagents

被引:268
作者
Fischer, C [1 ]
Fu, GC [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja0506509
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Ni/Pybox catalyst achieves the asymmetric cross-coupling of secondary α-bromo amides with organozinc reagents. The process tolerates a variety of functional groups and affords the desired product in good yield and in high enantiomeric excess. Copyright © 2005 American Chemical Society.
引用
收藏
页码:4594 / 4595
页数:2
相关论文
共 50 条
[31]   Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group [J].
Oelke, Alexander J. ;
Sun, Jianwei ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) :2966-2969
[32]   Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds [J].
Rosen, Brad M. ;
Quasdorf, Kyle W. ;
Wilson, Daniella A. ;
Zhang, Na ;
Resmerita, Ana-Maria ;
Garg, Neil K. ;
Percec, Virgil .
CHEMICAL REVIEWS, 2011, 111 (03) :1346-1416
[33]   Stereoconvergent and -divergent Synthesis of Tetrasubstituted Alkenes by Nickel-Catalyzed Cross-Couplings [J].
Zell, Daniel ;
Kingston, Cian ;
Jermaks, Janis ;
Smith, Sleight R. ;
Seeger, Natalie ;
Wassmer, Jana ;
Sirois, Lauren E. ;
Han, Chong ;
Zhang, Haiming ;
Sigman, Matthew S. ;
Gosselin, Francis .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (45) :19078-19090
[34]   Enantioselective nickel-catalyzed alkylative alkyne-aldehyde cross-couplings [J].
Nie, Ming ;
Fu, Wenzhen ;
Cao, Ziping ;
Tang, Wenjun .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10) :1322-1325
[35]   ORGN 309-Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents [J].
Smith, Sean W. ;
Fu, Gregory C. .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
[36]   Versatile OPiv-Supported Organozinc Reagents for Transition-Metal-Catalyzed Cross-Couplings [J].
Liu, Xingchen ;
Wang, Jixin ;
Li, Jie .
SYNLETT, 2022, 33 (17) :1688-1694
[37]   Nickel-catalyzed cross-couplings of unactivated alkyl halides and pseudohalides with organometallic compounds [J].
Netherton, MR ;
Fu, GC .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1525-1532
[38]   Mechanistic insights into photochemical nickel-catalyzed cross-couplings enabled by energy transfer [J].
Kancherla, Rajesh ;
Muralirajan, Krishnamoorthy ;
Maity, Bholanath ;
Karuthedath, Safakath ;
Kumar, Gadde Sathish ;
Laquai, Frederic ;
Cavallo, Luigi ;
Rueping, Magnus .
NATURE COMMUNICATIONS, 2022, 13 (01)
[39]   Mechanistic insights into photochemical nickel-catalyzed cross-couplings enabled by energy transfer [J].
Rajesh Kancherla ;
Krishnamoorthy Muralirajan ;
Bholanath Maity ;
Safakath Karuthedath ;
Gadde Sathish Kumar ;
Frédéric Laquai ;
Luigi Cavallo ;
Magnus Rueping .
Nature Communications, 13
[40]   Mild Cobalt-Catalyzed Negishi Cross-Couplings of (Hetero)arylzinc Reagents with (Hetero)aryl Halides [J].
Haas, Diana ;
Hammann, Jeffrey M. ;
Lutter, Ferdinand H. ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (11) :3809-3812