Ligand-Enabled Copper-Catalyzed Regio- and Stereoselective Allylboration of 1-Trifluoromethylalkenes

Kojima, Yuki; Nishii, Yuji; Hirano, Koji

Organic Letters, 2022, 24(40), 7450-7454

Number of Access:461（2025-07-17 20:08 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92685

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Title
Ligand-Enabled Copper-Catalyzed Regio- and Stereoselective Allylboration of 1-Trifluoromethylalkenes
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
Description
Kojima Y., Nishii Y., Hirano K.. Ligand-Enabled Copper-Catalyzed Regio- and Stereoselective Allylboration of 1-Trifluoromethylalkenes. Organic Letters. 24(40), 7450-7454, 14 October 2022; https://doi.org/10.1021/acs.orglett.2c03024.
Abstract
A copper-catalyzed regio- and stereoselective allylboration of 1-trifluoromethylalkenes with bis(pinacolato)diboron (pinB-Bpin) and allylic chlorides has been developed to form functionalized trifluoromethylated products with high diastereoselectivity. The key to success is the judicious choice of Cs2CO3 base and t-Bu-modified dppe-type ligand, which enables the otherwise challenging high catalyst turnover and suppression of the competing defluorination side reaction from an alkylcopper intermediate. The product derivatization of the resulting Bpin moiety can deliver diverse CF3-containing molecules with high stereochemical fidelity.
Publisher
American Chemical Society
Source Title
Organic Letters
Volume (Issue)
24(40)
Page
7450-7454
Date of Issued
2022-10-14
Language
English
Handle URL
https://hdl.handle.net/11094/92685
PISSN
15237060
eISSN
15237052
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.orglett.2c03024
Access Rights
open access
CopyRight
© 2022 American Chemical Society.
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.2c03024.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article