Palladium-Catalyzed α-Selective Halogenation of Triptycene Using Sulfur Directing Group

Ueno, Keisuke; Nishii, Yuji; Hirano, Koji et al.

Asian Journal of Organic Chemistry, 2023, 12(12), e202300588

Number of Access:122（2025-07-17 21:28 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/94009

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Title
Palladium-Catalyzed α-Selective Halogenation of Triptycene Using Sulfur Directing Group
Creator
CreatorName
Ueno, Keisuke
NRID
1000070773787 1000070773787
ORCID
0000-0002-6824-0639 0000-0002-6824-0639
researchmap permalink
y_nishii y_nishii
Scopus Author ID
55233363700 55233363700
CreatorName
Nishii, Yuji
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 activation
Halogenation
Palladium
Synthesis
Triptycenes
Description
This is the peer reviewed version of the following article: Ueno K., Nishii Y., Hirano K., et al. Palladium-Catalyzed α-Selective Halogenation of Triptycene Using Sulfur Directing Group. Asian Journal of Organic Chemistry 12, e202300588 (2023), which has been published in final form at https://doi.org/10.1002/ajoc.202300588. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
Abstract
Functionalized triptycene derivatives have attracted significant research interest because of their potential applications in many research fields. Although the conventional Diels-Alder reaction of anthracenes with benzynes has been a versatile synthetic tool for functionalized triptycenes, it is hardly possible to control the product regioselectivity. In this report, we demonstrate the selective synthesis of 1,8,13-trisubstituted triptycenes by Pd-catalyzed α-bromination. As for the directing group, SMe group was the most effective to facilitate the halogenation of the proximal three benzene rings. The obtained product was further derivatized through allylation and Rh-catalyzed hydroboration reactions.
Publisher
John Wiley and Sons Inc
Source Title
Asian Journal of Organic Chemistry
Volume (Issue)
12(12)
Page
e202300588
Date of Issued
2023-12-11
Language
English
Handle URL
https://hdl.handle.net/11094/94009
PISSN
21935807
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1002/ajoc.202300588
Access Rights
open access
CopyRight
© 2023 Wiley-VCH GmbH.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article