Highly Stereoselective Synthesis of 1,2-Disubstituted Indanes by Pd-Catalyzed Heck/Suzuki Sequence of Diarylmethyl Carbonates

Matsude, Akihiro; Hirano, Koji; Miura, Masahiro

Organic Letters, 2020, 22(8), 3190-3194

Number of Access:370（2025-07-17 20:50 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92704

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Title
Highly Stereoselective Synthesis of 1,2-Disubstituted Indanes by Pd-Catalyzed Heck/Suzuki Sequence 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
Description
Matsude A., Hirano K., Miura M.. Highly Stereoselective Synthesis of 1,2-Disubstituted Indanes by Pd-Catalyzed Heck/Suzuki Sequence of Diarylmethyl Carbonates. Organic Letters. 22(8), 3190-3194, (2020), 17 April 2020; © 2020 American Chemical Society. https://doi.org/10.1021/acs.orglett.0c00945.
Abstract
A palladium-catalyzed Mizoroki-Heck-type cyclization/Suzuki-Miyaura cross-coupling cascade of diarylmethyl carbonates with arylboronic acid derivatives has been developed to deliver the corresponding 1,2-disubstituted indanes in good yields with high diastereoselectivity (trans/cis > 20:1). The key to achieve the high chemoselectivity and stereoselectivity is the use of the tris[3,5-di(tert-butyl)-4-methoxyphenyl]phosphine (DTBMP) ligand of remote steric hindrance. Moreover, the asymmetric synthesis is possible by the enantiospecific, stereoinvertive reaction of the optically active starting substrates to form the chiral indanes with high stereochemical fidelity (>98% es).
Publisher
American Chemical Societyservice@acs.org
Source Title
Organic Letters
Volume (Issue)
22(8)
Page
3190-3194
Date of Issued
2020-04-17
Language
English
Handle URL
https://hdl.handle.net/11094/92704
PISSN
15237060
eISSN
15237052
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.orglett.0c00945
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, Organic Letters, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.0c00945.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article