Skip navigation
Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/20800
Title: Transition-Metal- A nd Light-Free Directed Amination of Remote Unactivated C(sp3)-H Bonds of Alcohols
Authors: Kurandina D.
Yadagiri, Dongari
Rivas M.
Kavun A.
Chuentragool P.
Hayama K.
Gevorgyan V.
Published in: Journal of the American Chemical Society
Abstract: Due to the great value of amino alcohols, new methods for their synthesis are in high demand. Abundant aliphatic alcohols represent the ideal feedstock for the method development toward this important motif. To date, transition-metal-catalyzed approaches for the directed remote amination of alcohols have been well established. Yet, they have certain disadvantages such as the use of expensive catalysts and limited scope. Very recently, transition-metal-free visible-light-induced radical approaches have emerged as new powerful tools for directed remote amination of alcohols. Relying on 1,5-HAT reactivity, these methods are limited to β-or δ- A mination only. Herein, we report a novel transitionmetal- A nd visible-light-free room-temperature radical approach for remote β-, γ-, and δ-C(sp3)-N bond formation in aliphatic alcohols using mild basic conditions and readily available diazonium salt reagents. © 2019 American Chemical Society. All rights reserved.
Citation: Journal of the American Chemical Society, 141(20): 8104-8109
URI: https://doi.org/10.1021/jacs.9b04189
http://repository.iitr.ac.in/handle/123456789/20800
Issue Date: 2020
Publisher: American Chemical Society
Keywords: Amination
Amines
Light
Transition metal compounds
Aliphatic alcohol
Basic conditions
Bond formation
Diazonium salts
High demand
Method development
Visible light
Visible light induced
Transition metals
alcohol derivative
carbon
diazonium compound
hydrogen
transition element
alcohol derivative
aminoalcohol
carbon
free radical
hydrogen
ketone
amination
Article
biotransformation
catalysis
chemical bond
chemical structure
controlled study
cyclization
electrophilicity
hydrogenation
hydrolysis
nucleophilicity
reaction optimization
regioselectivity
room temperature
synthesis
chemistry
synthesis
Alcohols
Amino Alcohols
Carbon
Cyclization
Free Radicals
Hydrogen
Ketones
ISSN: 27863
Author Scopus IDs: 55780442500
55875148200
57200315913
56404582300
48861112500
56684670400
7003570939
Author Affiliations: Kurandina, D., Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Rm. 4500, Chicago, IL 60607, United States
Yadagiri, D., Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Rm. 4500, Chicago, IL 60607, United States
Rivas, M., Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Rm. 4500, Chicago, IL 60607, United States
Kavun, A., Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Rm. 4500, Chicago, IL 60607, United States
Chuentragool, P., Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Rm. 4500, Chicago, IL 60607, United States
Hayama, K., Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Rm. 4500, Chicago, IL 60607, United States
Gevorgyan, V., Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Rm. 4500, Chicago, IL 60607, United States
Funding Details: We thank the National Institutes of Health (GM120281) and National Science Foundation (CHE-1663779) for the financial support of this work. We also thank visiting researchers Michael Buck and Mirela Sparano and undergraduate researcher Yana McAuliff for their help with preparation of starting materials for this work. National Science Foundation, NSF: 1936422, CHE-1663779; National Institutes of Health, NIH; National Institute of General Medical Sciences, NIGMS: R01GM120281
Corresponding Author: Gevorgyan, V.; Department of Chemistry, 845 W. Taylor Street, Rm. 4500, United States; email: vlad@uic.edu
Appears in Collections:Journal Publications [CY]

Files in This Item:
There are no files associated with this item.
Show full item record


Items in Repository are protected by copyright, with all rights reserved, unless otherwise indicated.