Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes

Kojima, Yuki; Nishii, Yuji; Hirano, Koji

Angewandte Chemie - International Edition, 2024, 63(24), e202403337

Number of Access:151（2025-07-17 20:09 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/95747

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Title
Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes
Creator
CreatorName
Kojima, Yuki
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
Subject
asymmetric catalysis
copper
fluorine molecule
hydrofunctionalization
trifluoromethylthio group
Description
Kojima Y., Nishii Y., Hirano K.. Asymmetric Synthesis of SCF₃₋Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes. Angewandte Chemie - International Edition , (2024); https://doi.org/10.1002/anie.202403337.
Abstract
A synthetic method for preparation of optically active trifluoromethylthio (SCF₃) compounds by a copper-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylthioalkenes with H-Bpin has been developed. The enantioselective hydrocupration of an in situ generated CuH species and subsequent boration reaction generate a chiral SCF₃₋containing alkylboronate, of which Bpin moiety can be further transformed to deliver various optically active SCF₃ molecules. Computational studies suggest that the SCF₃ group successfully controls the regioselectivity in the reaction.
Publisher
John Wiley and Sons Inc
Source Title
Angewandte Chemie - International Edition
Volume (Issue)
63(24)
Page
e202403337
Date of Issued
2024-05-10
Language
English
Handle URL
https://hdl.handle.net/11094/95747
PISSN
14337851
eISSN
15213773
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1002/anie.202403337
Access Rights
open access
CopyRight
This article is licensed under a Creative Commons Attribution 4.0 International License.
oaire:version
Version of Record
Category
学術雑誌論文 Journal Article