Palladium-Catalyzed Intramolecular Mizoroki-Heck-Type Reaction of Diarylmethyl Carbonates

Matsude, Akihiro; Hirano, Koji; Miura, Masahiro

Advanced Synthesis and Catalysis, 2020, 362(3), 518-522

Number of Access:143（2025-07-18 02:10 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92735

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Title
Palladium-Catalyzed Intramolecular Mizoroki-Heck-Type Reaction of Diarylmethyl Carbonates
Creator
CreatorName
Matsude, Akihiro
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
asymmetric catalysis
indanes
kinetic resolution
Mizoroki-Heck reaction
palladium
Description
This is the accepted version of the following article: Matsude A., Hirano K., Miura M.. Palladium-Catalyzed Intramolecular Mizoroki-Heck-Type Reaction of Diarylmethyl Carbonates. Advanced Synthesis and Catalysis 362, 518 (2020), which has been published in final form at https://doi.org/10.1002/adsc.201901398. 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 palladium-catalyzed intramolecular Mizoroki-Heck-type reaction of diarylmethyl tert-butyl carbonates has been developed. The reaction proceeds under external base-free, neutral conditions to form the corresponding methyleneindanes in good yields only with liberation of CO2 and tBuOH. The resulting exo-methylene moiety is reactive and thus a good synthetic handle for further manipulations. Additionally, the asymmetric synthesis is also possible through a Pd/chiral Mandyphos ligand-mediated kinetic resolution. To the best of our knowledge, this is the first successful example of catalytic enantioselective Mizoroki-Heck-type reaction of secondary benzyl electrophiles. (Figure presented.).
Publisher
Wiley-VCH
Source Title
Advanced Synthesis and Catalysis
Volume (Issue)
362(3)
Page
518-522
Date of Issued
2020-02-06
Language
English
Handle URL
https://hdl.handle.net/11094/92735
PISSN
16154150
eISSN
16154169
NCID
AA11553845
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1002/adsc.201901398
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