Divergent synthesis of isonitriles and nitriles by palladium- catalyzed benzylic substitution with TMSCN

Hirano, Koji; Miura, Masahiro; Asai, Kento

Journal of Organic Chemistry, 2020, 85(19), 12703-12714

Number of Access:161（2025-06-07 02:33 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92700

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Title
Divergent synthesis of isonitriles and nitriles by palladium- catalyzed benzylic substitution with TMSCN
Creator
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
CreatorName
Asai, Kento
Description
Hirano K., Miura M., Asai K.. Divergent synthesis of isonitriles and nitriles by palladium- catalyzed benzylic substitution with TMSCN. Journal of Organic Chemistry. 85(19), 12703-12714, (2020), 2 October 2020; © 2020 American Chemical Society. https://doi.org/10.1021/acs.joc.0c01861.
Abstract
Ligand-controlled palladium-catalyzed divergent synthesis of isonitriles and nitriles from benzylic carbonates and TMSCN has been developed. The BINAP- or DPEphos-ligated palladium catalyst selectively provides the corresponding benzylic isonitriles, whereas their regioisomers, benzylic nitriles, are formed exclusively under phosphine ligand-free conditions. Mechanistic studies reveal that isonitrile is the primary product under both conditions, but it is isomerized into nitrile in the absence of ancillary phosphine ligands.
Publisher
American Chemical Society
Source Title
Journal of Organic Chemistry
Volume (Issue)
85(19)
Page
12703-12714
Date of Issued
2020-10-02
Language
English
Handle URL
https://hdl.handle.net/11094/92700
PISSN
00223263
eISSN
15206904
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.joc.0c01861
Access Rights
open access
CopyRight
© 2020 American Chemical Society.
This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in, Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.joc.0c01861.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article