Journal of Organic Chemistry, volume 84, issue 20, pages 13065-13072
Development of an Imine Chaperone for Selective C–H Functionalization of Alcohols via Radical Relay
Publication type: Journal Article
Publication date: 2019-09-12
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
The design of a radical relay chaperone to promote selective C-H functionalizations is described. A saccharin-based imine was found to be uniquely suited to effect C-H amination of alcohols via an in situ generated hemiaminal. This radical chaperone facilitates the mild generation of an N-centered radical while also directing its regioselective H atom transfer (HAT) to the β carbon of an alcohol. Upon β C-H halogenation, aminocyclization, and reductive cleavage, an NH2 is formally added vicinal to an alcohol. The development, synthetic utility, and chemo-, regio-, and stereoselectivity of this imine chaperone-mediated C-H amination is presented herein.
Top-30
Citations by journals
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Chemistry - An Asian Journal
1 publication, 12.5%
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Israel Journal of Chemistry
1 publication, 12.5%
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Advanced Synthesis and Catalysis
1 publication, 12.5%
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Journal of Organic Chemistry
1 publication, 12.5%
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Organic Letters
1 publication, 12.5%
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Organic Chemistry Frontiers
1 publication, 12.5%
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Russian Chemical Reviews
1 publication, 12.5%
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1
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Citations by publishers
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1
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4
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Wiley
4 publications, 50%
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American Chemical Society (ACS)
2 publications, 25%
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Royal Society of Chemistry (RSC)
1 publication, 12.5%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 12.5%
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4
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Nakafuku K. M. et al. Development of an Imine Chaperone for Selective C–H Functionalization of Alcohols via Radical Relay // Journal of Organic Chemistry. 2019. Vol. 84. No. 20. pp. 13065-13072.
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Nakafuku K. M., Twumasi R. K., Vanitcha A., Wappes E. A., Namitharan K., Bekkaye M., Nagib D. A. Development of an Imine Chaperone for Selective C–H Functionalization of Alcohols via Radical Relay // Journal of Organic Chemistry. 2019. Vol. 84. No. 20. pp. 13065-13072.
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TY - JOUR
DO - 10.1021/acs.joc.9b02052
UR - https://doi.org/10.1021/acs.joc.9b02052
TI - Development of an Imine Chaperone for Selective C–H Functionalization of Alcohols via Radical Relay
T2 - Journal of Organic Chemistry
AU - Twumasi, Raymond K
AU - Vanitcha, Avassaya
AU - Wappes, Ethan A.
AU - Bekkaye, Mathieu
AU - Nagib, David A
AU - Nakafuku, Kohki M
AU - Namitharan, K.
PY - 2019
DA - 2019/09/12 00:00:00
PB - American Chemical Society (ACS)
SP - 13065-13072
IS - 20
VL - 84
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2019_Nakafuku,
author = {Raymond K Twumasi and Avassaya Vanitcha and Ethan A. Wappes and Mathieu Bekkaye and David A Nagib and Kohki M Nakafuku and K. Namitharan},
title = {Development of an Imine Chaperone for Selective C–H Functionalization of Alcohols via Radical Relay},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.joc.9b02052},
number = {20},
pages = {13065--13072},
doi = {10.1021/acs.joc.9b02052}
}
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Nakafuku, Kohki M., et al. “Development of an Imine Chaperone for Selective C–H Functionalization of Alcohols via Radical Relay.” Journal of Organic Chemistry, vol. 84, no. 20, Sep. 2019, pp. 13065-13072. https://doi.org/10.1021/acs.joc.9b02052.