Synthesis of Seven-Membered Benzolactones by Nickel-Catalyzed C−H Coupling of Benzamides with Oxetanes

Xu, Shibo; Takamatsu, Kazutaka; Hirano, Koji et al.

Chemistry - A European Journal, 2019, 25(40), 9400-9404

Number of Access:117（2025-07-17 20:47 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92741

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Title
Synthesis of Seven-Membered Benzolactones by Nickel-Catalyzed C−H Coupling of Benzamides with Oxetanes
Creator
CreatorName
Xu, Shibo
CreatorName
Takamatsu, Kazutaka
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
Subject
C−H coupling
lactones
medium-sized rings
nickel
oxetanes
Description
This is the accepted version of the following article: Xu S., Takamatsu K., Hirano K., et al. Synthesis of Seven-Membered Benzolactones by Nickel-Catalyzed C−H Coupling of Benzamides with Oxetanes. Chemistry - A European Journal 25, 9400 (2019), which has been published in final form at https://doi.org/10.1002/chem.201900543. This article may be used for non-commercialpurposes in accordance with the Wiley Self-ArchivingPolicy [https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html]
Abstract
A NiCl2(PEt3)2-catalyzed regioselective C−H coupling of 8-aminoquinoline-derived benzamides with oxetanes has been developed. The reaction proceeds with concomitant removal of the 8-aminoquinoline auxiliary to directly form the corresponding seven-membered benzolactones, which frequently occur in natural products and bioactive molecules. Additionally, no stereochemical erosion is observed during the course of the reaction, and the use of enantioenriched and substituted oxetane thus provides a new avenue to the optically active benzolactone.
Publisher
Wiley-VCH
Source Title
Chemistry - A European Journal
Volume (Issue)
25(40)
Page
9400-9404
Date of Issued
2019-07-17
Language
English
Handle URL
https://hdl.handle.net/11094/92741
PISSN
09476539
eISSN
15213765
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1002/chem.201900543
Access Rights
open access
CopyRight
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article