Efficient Amination of Activated and Non-Activated C(sp3)-H Bonds with a Simple Iron-Phenanthroline Catalyst

被引:30
作者
Jarrige, Lucie [1 ]
Zhou, Zijun [1 ]
Hemming, Marcel [1 ]
Meggers, Eric [1 ]
机构
[1] Philipps Univ Marburg, Fachbereich Chem, Hans Meerwein Str 4, D-35043 Marburg, Germany
关键词
catalysis; C-H amination; imidazolidin-2-ones; iron; nitrene; C-H AMINATION; NITRENE TRANSFER-REACTIONS; ORGANIC-SYNTHESIS; METAL; FUNCTIONALIZATION; CHALLENGES; COMPLEXES; ANALOGS; AZIDES; SCOPE;
D O I
10.1002/anie.202013687
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A readily available catalyst consisting of iron dichloride in combination with 1,10-phenanthroline catalyzes the ring-closing C-H amination of N-benzoyloxyurea to form imidazolidin-2-ones in high yields. The C-H amination reaction is very general and applicable to benzylic, allylic, propargylic, and completely non-activated aliphatic C(sp(3))-H bonds, and it also works for C(sp(2))-H bonds. The surprisingly simple method can be performed under open flask conditions.
引用
收藏
页码:6314 / 6319
页数:6
相关论文
共 71 条
[1]   Recent applications of C-H functionalization in complex natural product synthesis [J].
Abrams, Dylan J. ;
Provencher, Philip A. ;
Sorensen, Erik J. .
CHEMICAL SOCIETY REVIEWS, 2018, 47 (23) :8925-8967
[2]   Iron-Catalyzed Intramolecular Aminations of C(sp3)-H Bonds in Alkylaryl Azides [J].
Alt, Isabel T. ;
Guttroff, Claudia ;
Plietker, Bernd .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (35) :10582-10586
[3]   Iron-Catalyzed Intramolecular C(sp2)-H Amination [J].
Alt, Isabel T. ;
Plietker, Bernd .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (04) :1519-1522
[4]  
[Anonymous], 2018, ANGEW CHEM, V130, P12123
[5]  
[Anonymous], 2018, ANGEW CHEM, V130, P64
[6]  
[Anonymous], 2012, ANGEW CHEM, V124, P7498
[7]  
[Anonymous], 2008, ANGEW CHEM, V120, P3363
[8]  
[Anonymous], 2017, ANGEW CHEM, V129, P10718
[9]  
[Anonymous], 2020, ANGEW CHEM, DOI [10.1002/ANGE.202013499, DOI 10.1002/ANGE.202013499]
[10]  
[Anonymous], 2016, ANGEW CHEM, V128, P1542