TY - JOUR
T1 - Transition-Metal- A nd Light-Free Directed Amination of Remote Unactivated C(sp3)-H Bonds of Alcohols
AU - Kurandina, Daria
AU - Yadagiri, Dongari
AU - Rivas, Monica
AU - Kavun, Aleksei
AU - Chuentragool, Padon
AU - Hayama, Keiichi
AU - Gevorgyan, Vladimir
N1 - Funding Information:
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.
Publisher Copyright:
© 2019 American Chemical Society. All rights reserved.
PY - 2020
Y1 - 2020
N2 - 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.
AB - 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.
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U2 - 10.1021/jacs.9b04189
DO - 10.1021/jacs.9b04189
M3 - Article
C2 - 31046256
AN - SCOPUS:85066883048
SN - 0002-7863
VL - 141
SP - 8104
EP - 8109
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 20
ER -