Enantioselective Aluminum-Free Alkene Hydroarylations through C-H Activation by a Chiral Nickel/JoSPOphos Manifold

被引：71
作者：
Loup, Joachim [1 ]
Mueller, Valentin [1 ]
Ghorai, Debasish [1 ,2 ]
Ackermann, Lutz [1 ,2 ]
机构：
[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
[2] Univ Pavia, Dept Chem, Viale Taramelli 10, I-27100 Pavia, Italy
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 06期
关键词：
aluminum-free; asymmetric catalysis; C-H activation; nickel; SPOs; BOND ACTIVATION; SELECTIVE ALKENYLATION; PHOSPHINE OXIDES; METAL; FUNCTIONALIZATION; ALKYNES; ALKYLATION; MECHANISM; HYDROHETEROARYLATION; HETEROCYCLES;
D O I：
10.1002/anie.201813191
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Highly enantioselective nickel-catalyzed alkene endo-hydroarylations were accomplished with full selectivity by organometallic C-H activation. The asymmetric assembly of chiral six-membered scaffolds proved viable in the absence of pyrophoric organoaluminum reagents within an unprecedented nickel/JoSPOphos manifold.
引用
收藏
页码：1749 / 1753
页数：5
相关论文
共 101 条
[61]   Synthesis of potent bicyclic bisarylimidazole c-jun N-terminal kinase inhibitors by catalytic C-H bond activation [J].
Rech, Jason C. ;
Yato, Michihisa ;
Duckett, Derek ;
Ember, Brian ;
LoGrasso, Philip V. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (03) :490-491
[62]  
Rouquet G., 2013, ANGEW CHEM, V125, P11942, DOI DOI 10.1002/ANGE.201301451
[63]   Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups [J].
Rouquet, Guy ;
Chatani, Naoto .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) :11726-11743
[64]   Ruthenium(II)-Catalyzed meta C-H Mono- and Difluoromethylations by Phosphine/Carboxylate Cooperation [J].
Ruan, Zhixiong ;
Zhang, Shou-Kun ;
Zhu, Cuiju ;
Ruth, Paul Niklas ;
Stalke, Dietmar ;
Ackermann, Lutz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (08) :2045-2049
[65]   Nickel-Catalyzed C-H Alkynylation of Anilines: Expedient Access to Functionalized Indoles and Purine Nucleobases [J].
Ruan, Zhixiong ;
Lackner, Sebastian ;
Ackermann, Lutz .
ACS CATALYSIS, 2016, 6 (07) :4690-4693
[66]   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
[67]   Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis [J].
Satoh, Tetsuya ;
Miura, Masahiro .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) :11212-11222
[68]  
Satyanarayana T., 2009, ANGEW CHEM, V121, P464
[69]   Nonlinear Effects In Asymmetric Catalysis [J].
Satyanarayana, Tummanapalli ;
Abraham, Susan ;
Kagan, Henri B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :456-494
[70]   Anti-Markovnikov Hydroheteroarylation of Unactivated Alkenes with Indoles, Pyrroles, Benzofurans, and Furans Catalyzed by a Nickel-N-Heterocyclic Carbene System [J].
Schramm, York ;
Takeuchi, Makoto ;
Semba, Kazuhiko ;
Nakao, Yoshiaki ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (38) :12215-12218
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