Palladium-Catalyzed Benzylic Silylation of Diarylmethyl Carbonates with Silylboranes under Base-Free Conditions

Asai, Kento; Hirano, Koji; Miura, Masahiro

European Journal of Organic Chemistry, 2022, 2022(17), e202101535

Number of Access:147（2025-07-17 20:42 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92734

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Title
Palladium-Catalyzed Benzylic Silylation of Diarylmethyl Carbonates with Silylboranes under Base-Free Conditions
Creator
CreatorName
Asai, Kento
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
Benzylic substitution
Palladium
Silylation
Silylborane
Synthetic method
Description
Asai K., Hirano K., Miura M.. Palladium-Catalyzed Benzylic Silylation of Diarylmethyl Carbonates with Silylboranes under Base-Free Conditions. European Journal of Organic Chemistry 2022, e202101535 (2022); https://doi.org/10.1002/ejoc.202101535.
Abstract
A palladium-catalyzed benzylic silylation of diarylmethyl carbonates with silylboranes has been developed. The reaction proceeds smoothly even under external base-free conditions, and the corresponding benzylic silanes are formed in good to high yields. The obtained benzyl silane derivatives can work as the benzylic nucleophiles by the action of a suitable fluoride source and react with some carbon electrophiles to deliver the corresponding benzylic C−C cross-coupled products. Additionally, while still preliminary, the allylic silylation of the isoelectronic allylic carbonates is also achieved.
Publisher
John Wiley and Sons Inc
Source Title
European Journal of Organic Chemistry
Volume (Issue)
2022(17)
Page
e202101535
Date of Issued
2022-05-06
Language
English
Handle URL
https://hdl.handle.net/11094/92734
PISSN
1434193X
eISSN
10990690
NCID
AA1118165X
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1002/ejoc.202101535
Access Rights
open access
CopyRight
© 2022 Wiley-VCH GmbH
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article