中文版 | English
Title

Chiral Iron Porphyrins Catalyze Enantioselective Intramolecular C(sp(3))-H Bond Amination Upon Visible-Light Irradiation

Author
Corresponding AuthorDang, Li; Liu, Yungen; Che, Chi-Ming
Publication Years
2023-02-01
DOI
Source Title
ISSN
1433-7851
EISSN
1521-3773
Abstract
Iron-catalyzed asymmetric amination of C(sp(3))-H bonds is appealing for synthetic applications due to the biocompatibility and high earth abundance of iron, but examples of such reactions are sparse. Herein we describe chiral iron complexes of meso- and beta-substituted-porphyrins that can catalyze asymmetric intramolecular C(sp(3))-H amination of aryl and arylsulfonyl azides to afford chiral indolines (29 examples) and benzofused cyclic sulfonamides (17 examples), respectively, with up to 93 % ee (yield: up to 99 %) using 410 nm light under mild conditions. Mechanistic studies, including DFT calculations, for the reactions of arylsulfonyl azides reveal that the Fe(NSO2Ar) intermediate generated in situ under photochemical conditions reacts with the C(sp(3))-H bond through a stepwise hydrogen atom transfer/radical rebound mechanism, with enantioselectivity arising from cooperative noncovalent interactions between the Fe(NSO2Ar) unit and the peripheral substituents of the chiral porphyrin scaffold.
Keywords
URL[Source Record]
Indexed By
Language
English
Important Publications
NI Journal Papers
SUSTech Authorship
First ; Corresponding
Funding Project
National Natural Science Foundation of China["NSFC 21871127","91856203"] ; Shenzhen Science and Technology Innovation Commission[JCYJ20190809141203613] ; General Research Fund from the Hong Kong Research Grants Council["17301817","17304019"]
WOS Research Area
Chemistry
WOS Subject
Chemistry, Multidisciplinary
WOS Accession No
WOS:000937297300001
Publisher
ESI Research Field
CHEMISTRY
Data Source
Web of Science
Citation statistics
Cited Times [WOS]:2
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/502120
DepartmentDepartment of Chemistry
Affiliation
1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
2.Univ Hong Kong, State Key Lab Synthet Chem, Hong Kong, Peoples R China
3.Univ Hong Kong, Dept Chem, Hong Kong, Peoples R China
4.HKU Shenzhen Inst Res & Innovat, Shenzhen 518057, Guangdong, Peoples R China
5.Hong Kong Sci & Technol Pk, Lab Synthet Chem & Chem Biol Ltd, New Terr, Units 1503 1511,15-F,Bldg 17 W, Hong Kong, Peoples R China
6.Shantou Univ, Dept Chem, Shantou 515063, Guangdong, Peoples R China
7.Shantou Univ, Key Lab Preparat & Applicat Ordered Struct Mat Gua, Shantou 515063, Guangdong, Peoples R China
8.Chem & Chem Engn Guangdong Lab, Shantou 515063, Guangdong, Peoples R China
First Author AffilicationDepartment of Chemistry
Corresponding Author AffilicationDepartment of Chemistry
First Author's First AffilicationDepartment of Chemistry
Recommended Citation
GB/T 7714
Wang, Hua-Hua,Shao, Hui,Huang, Guanglong,et al. Chiral Iron Porphyrins Catalyze Enantioselective Intramolecular C(sp(3))-H Bond Amination Upon Visible-Light Irradiation[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023.
APA
Wang, Hua-Hua.,Shao, Hui.,Huang, Guanglong.,Fan, Jianqiang.,To, Wai-Pong.,...&Che, Chi-Ming.(2023).Chiral Iron Porphyrins Catalyze Enantioselective Intramolecular C(sp(3))-H Bond Amination Upon Visible-Light Irradiation.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
MLA
Wang, Hua-Hua,et al."Chiral Iron Porphyrins Catalyze Enantioselective Intramolecular C(sp(3))-H Bond Amination Upon Visible-Light Irradiation".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023).
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