Expedient Iron-Catalyzed C-H Allylation/ Alkylation by Triazole Assistance with Ample Scope

被引:158
作者
Cera, Gianpiero [1 ]
Haven, Tobias [1 ]
Ackermann, Lutz [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
基金
欧洲研究理事会;
关键词
alkylation; allylation; C-H activation; iron; triazoles; LATE-STAGE DIVERSIFICATION; CARBON-CARBON BONDS; COUPLING REACTIONS; ARYLATION; CARBOXAMIDES; HYDROGEN; FUNCTIONALIZATION; ACTIVATION; C(SP(2))-H; ARENES;
D O I
10.1002/anie.201509603
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Triazole assistance set the stage for a unified strategy for the iron-catalyzed C-H allylation of arenes, heteroarenes, and alkenes with ample scope. The versatile catalyst also proved competent for site-selective methylation, benzylation, and alkylation with challenging primary and secondary halides. Triazole-assisted C-H activation proceeded chemo-, site-, and diastereo-selectively, and the modular TAM directing group was readily removed in a traceless fashion under exceedingly mild reaction conditions.
引用
收藏
页码:1484 / 1488
页数:5
相关论文
共 85 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2]   Cobalt-Catalyzed C-H Arylations, Benzylations, and Alkylations with Organic Electrophiles and Beyond [J].
Ackermann, Lutz .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) :8948-8954
[3]   Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines [J].
Ackermann, Lutz ;
Hofmann, Nora ;
Vicente, Ruben .
ORGANIC LETTERS, 2011, 13 (07) :1875-1877
[4]   Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877
[5]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[6]   Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].
Ackermann, Lutz ;
Novak, Petr ;
Vicente, Ruben ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048
[7]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311
[8]   Triazole-Assisted Ruthenium-Catalyzed C-H Arylation of Aromatic Amides [J].
Al Mamari, Hamad H. ;
Diers, Emelyne ;
Ackermann, Lutz .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (31) :9739-9743
[9]  
[Anonymous], 2009, ANGEW CHEM
[10]  
[Anonymous], 2013, ANGEW CHEM