Synthesis of α-Trifluoromethylamines by Cu-Catalyzed Regio- and Enantioselective Hydroamination of 1-Trifluoromethylalkenes

Takata, Tatsuaki; Hirano, Koji; Miura, Masahiro

Organic Letters, 2019, 21(11), 4284-4288

Number of Access:365（2025-07-17 21:06 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92707

Link to primary information 

File Format Terms of use Size Views Date.Available Description information
OrgLett_21_11_4284 pdf None 402 KB 112 2023.10.06  

Item Information

Output File Export EndNote Basic Export Mendeley

Title
Synthesis of α-Trifluoromethylamines by Cu-Catalyzed Regio- and Enantioselective Hydroamination of 1-Trifluoromethylalkenes
Creator
CreatorName
Takata, Tatsuaki
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
Takata T., Hirano K., Miura M.. Synthesis of α-Trifluoromethylamines by Cu-Catalyzed Regio- and Enantioselective Hydroamination of 1-Trifluoromethylalkenes. Organic Letters. 21(11), 4284-4288, (2019),7 June 2019; © 2019 American Chemical Society. https://doi.org/10.102/acs.orglett.9b01471.
Abstract
A copper-catalyzed regioselective net hydroamination of 1-trifluoromethylalkenes with hydrosilanes and hydroxylamines has been developed. The judicious choice of ligand and additive suppresses the conceivable but undesired β-F elimination of an α-CF3-substituted organocopper intermediate, leading to targeted α-trifluoromethylamines in good yields with excellent regioselectivity. Additionally, with an appropriate chiral bisphosphine ligand, the enantioselective reaction is also possible to deliver optically active α-trifluoromethylamines of high potential in medicinal and pharmaceutical chemistry.
Publisher
American Chemical Societyservice@acs.org
Source Title
Organic Letters
Volume (Issue)
21(11)
Page
4284-4288
Date of Issued
2019-01-07
Language
English
Handle URL
https://hdl.handle.net/11094/92707
PISSN
15237060
eISSN
15237052
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.orglett.9b01471
Access Rights
open access
CopyRight
© 2019 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.9b01471.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article