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

Kohki M Nakafuku 1
Raymond K Twumasi 1
Avassaya Vanitcha 1
Ethan A. Wappes 1
K. Namitharan 1
Mathieu Bekkaye 1
David A Nagib 1
Publication typeJournal Article
Publication date2019-09-12
Q2
Q1
SJR0.724
CiteScore6.2
Impact factor3.3
ISSN00223263, 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.
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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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 - Nakafuku, Kohki M
AU - Twumasi, Raymond K
AU - Vanitcha, Avassaya
AU - Wappes, Ethan A.
AU - Namitharan, K.
AU - Bekkaye, Mathieu
AU - Nagib, David A
PY - 2019
DA - 2019/09/12
PB - American Chemical Society (ACS)
SP - 13065-13072
IS - 20
VL - 84
PMID - 31513401
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Nakafuku,
author = {Kohki M Nakafuku and Raymond K Twumasi and Avassaya Vanitcha and Ethan A. Wappes and K. Namitharan and Mathieu Bekkaye and David A Nagib},
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}
}
MLA
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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.
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