Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives

Nishino, Soshi; Hirano, Koji; Miura, Masahiro

Organic Letters, 2019, 21(12), 4759-4762

Number of Access:343（2025-07-17 20:59 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92705

Link to primary information 

File Format Terms of use Size Views Date.Available Description information
OrgLett_21_12_4759 pdf None 425 KB 85 2023.10.06  

Item Information

Output File Export EndNote Basic Export Mendeley

Title
Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives
Creator
CreatorName
Nishino, Soshi
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
Nishino S., Hirano K., Miura M.. Copper-Catalyzed Electrophilic Amination of gem-Diborylalkanes with Hydroxylamines Providing α-Aminoboronic Acid Derivatives. Organic Letters. 21(12), 4759-4762, (2019), 21 June 2019; © 2019 American Chemical Society. https://doi.org/10.1021/acs.orglett.9b01640.
Abstract
A copper-catalyzed electrophilic amination of gem-diborylalkanes with hydroxylamines has been developed. The key to its success is the use of the Me3Si-modified 1,2-bis(diphenylphosphino)benzene ligand. Additionally, the reactivity of neopentylglycol derivatives compared to that of commonly used pinacol-derived ones is found to be higher, particularly in the case of relatively sterically congested substrates. The copper catalysis presented here enables the first successful catalytic carbon-heteroatom bond forming reaction of gem-diborylalkanes to form the corresponding α-aminoboronic acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry.
Publisher
American Chemical Societyservice@acs.org
Source Title
Organic Letters
Volume (Issue)
21(12)
Page
4759-4762
Date of Issued
2019-06-21
Language
English
Handle URL
https://hdl.handle.net/11094/92705
PISSN
15237060
eISSN
15237052
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.orglett.9b01640
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.9b01640.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article