Nickel-Catalyzed Regio- And Stereospecific C-H Coupling of Benzamides with Aziridines

Xu, Shibo; Hirano, Koji; Miura, Masahiro

Organic Letters, 2021, 23(14), 5471-5475

Number of Access:529（2025-07-17 20:38 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92696

Link to primary information 

File Format Terms of use Size Views Date.Available Description information
OrgLett_23_14_5471 pdf None 706 KB 181 2023.10.05  

Item Information

Output File Export EndNote Basic Export Mendeley

Title
Nickel-Catalyzed Regio- And Stereospecific C-H Coupling of Benzamides with Aziridines
Creator
CreatorName
Xu, Shibo
NRID
1000070532696 1000070532696
ORCID
0000-0001-9752-1985 0000-0001-9752-1985
researchmap permalink
koj koj
Scopus Author ID
7402407063 7402407063
CreatorName
Hirano, Koji
NRID
1000020183626 1000020183626
ORCID
0000-0001-8288-6439 0000-0001-8288-6439
researchmap permalink
read0013936 read0013936
Scopus Author ID
7402799909 7402799909
CreatorName
Miura, Masahiro
Description
Xu S., Hirano K., Miura M.. Nickel-Catalyzed Regio- And Stereospecific C-H Coupling of Benzamides with Aziridines. Organic Letters. 23(14), 5471-5475, (2021), 16 July 2021; © 2021 American Chemical Society. https://doi.org/10.1021/acs.orglett.1c01821.
Abstract
A nickel-catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with aryl- and alkyl-substituted aziridines has been disclosed. The current strategy provides direct access to benzolactams by the C-H alkylation-intramolecular amidation cascade event with the concomitant removal of the aminoquinoline auxiliary. The regioselectivity of ring opening of aziridines can be controlled by the substituents. The reaction with chiral aziridines proceeds with inversion of configuration, thus suggesting an SN2-type nucleophilic ring-opening pathway.
Publisher
American Chemical Society
Source Title
Organic Letters
Volume (Issue)
23(14)
Page
5471-5475
Date of Issued
2021-07-16
Language
English
Handle URL
https://hdl.handle.net/11094/92696
PISSN
15237060
eISSN
15237052
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.orglett.1c01821
Access Rights
open access
CopyRight
© 2021 American Chemical Society.
This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in,　Organic Letters, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.1c01821.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article