| Title | Chiral Iron Porphyrins Catalyze Enantioselective Intramolecular C(sp(3))-H Bond Amination Upon Visible-Light Irradiation |
| Author | |
| Corresponding Author | Dang, 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 Type | Journal Article |
| Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/502120 |
| Department | Department 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 Affilication | Department of Chemistry |
| Corresponding Author Affilication | Department of Chemistry |
| First Author's First Affilication | Department 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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