Regio- and Stereoselective Iodoamination of Ferrocene-Containing Allenylphosphonates: Synthesis of Multifunctional Tetrasubstituted Allylic Amines and Allylic Azides

被引:2
作者
Guo, Le [1 ,2 ]
Zhao, Wanrong [1 ]
Gao, Yanpeng [2 ]
Wu, Meimei [2 ]
Chen, Shufeng [1 ]
机构
[1] Inner Mongolia Univ, Dept Chem & Chem Engn, Hohhot 010021, Peoples R China
[2] Ordos Inst Technol, Coll Chem Engn, Ordos 017000, Peoples R China
基金
中国国家自然科学基金;
关键词
BIOORGANOMETALLIC CHEMISTRY; STRUCTURAL DIVERSITY; PALLADIUM; ALLENES; HYDROAMINATION; FERROCENYLALLENE; HETEROCYCLES; COMPLEXES; CATALYSIS; AZIDATION;
D O I
10.1021/acs.joc.3c02686
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and practical methodology for the regio- and stereoselective synthesis of multifunctional tetrasubstituted allylic amines and azides based on iodoamination of ferrocene-containing allenylphosphonates with anilines and sodium azide is described. A tetrasubstituted olefin moiety, as well as an iodine atom, a phosphonate, and a ferrocene group, are installed to the allylic amine motif simultaneously in moderate to good yields.
引用
收藏
页码:1956 / 1966
页数:11
相关论文
共 55 条
[1]   Highly functionalised (γ-azido/γ-fluoro-β-iodo/)vinyl derivatives from phosphorus based allenes or allenoates: I•••O halogen bonding interactions [J].
Anitha, Mandala ;
Swamy, K. C. Kumara .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (23) :5736-5748
[2]   Bioorganometallic Chemistry and Malaria [J].
Biot, Christophe ;
Dive, Daniel .
MEDICINAL ORGANOMETALLIC CHEMISTRY, 2010, 32 :155-193
[3]   A New Age for Iron: Antitumoral Ferrocenes [J].
Braga, Susana S. ;
Silva, Artur M. S. .
ORGANOMETALLICS, 2013, 32 (20) :5626-5639
[4]   Oxidative Allylic Amination Reactions of Unactivated Olefins - At the Frontiers of Palladium and Selenium Catalysis [J].
Breder, Alexander .
SYNLETT, 2014, 25 (07) :899-904
[5]   Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates [J].
Butt, Nicholas A. ;
Zhang, Wanbin .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) :7929-7967
[6]   Allylic azides: synthesis, reactivity, and the Winstein rearrangement [J].
Carlson, Angela S. ;
Topczewski, Joseph J. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (18) :4406-4429
[7]   Regio- and Stereoselective Synthesis of Ferrocene-Containing β-Iodoallylic Esters and Ethers from the Iodofunctionalization of Ferrocenylallene with Carboxylic Acids, Phenols, and Alcohols [J].
Chen, Shufeng ;
Zhang, Hongli ;
Yan, Qing ;
Wang, Chenjun ;
Han, Fei ;
Zhang, Kaixin ;
Zhao, Haiying ;
Li, Baoguo .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12) :5503-5510
[8]   Palladium-Catalyzed Regio- and Stereoselective Arylesterification of Ferrocenylallene: A Synthetic Route to Ferrocene-Containing Disubstituted E-Allylic Esters [J].
Chen, Shufeng ;
Gao, Zhenlong ;
Zhao, Haiying ;
Li, Baoguo .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) :1481-1486
[9]   Palladium-catalyzed three-component reaction of ferrocenyl allenes, aryl iodides and active methylene compounds: regio- and stereoselective synthesis of (E)-alkenylferrocenes [J].
Chen, Shufeng ;
Gao, Zhenlong ;
Wu, Chao ;
Zhao, Haiying ;
Li, Baoguo .
RSC ADVANCES, 2013, 3 (44) :21326-21330
[10]   Iodine-Mediated Highly Regio- and Stereoselective Iodoamination of Ferrocenyl Allene: An Approach for the Synthesis of Ferrocene-Containing Allylic Amines [J].
Chen, Shufeng ;
Yan, Qing ;
Zhao, Haiying ;
Li, Baoguo .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (10) :5085-5089