Open Access
Catalytic β C–H amination via an imidate radical relay
Leah M Stateman
1, 2, 3, 4, 5
,
Ethan A. Wappes
1, 2, 3, 4, 5
,
Kohki M Nakafuku
1
,
Kara M Edwards
1, 2, 3, 4, 5
,
David A Nagib
1, 2, 3, 4, 5
3
Department of Chemistry and Biochemistry
4
Columbus
|
5
Usa
|
Publication type: Journal Article
Publication date: 2019-01-17
scimago Q1
wos Q1
SJR: 2.138
CiteScore: 12.6
Impact factor: 7.4
ISSN: 20416520, 20416539
PubMed ID:
30996986
General Chemistry
Abstract
The first catalytic strategy to harness imidate radicals for C–H functionalization has been developed. This iodine-catalyzed approach enables β C–H amination of alcohols by an imidate-mediated radical relay. In contrast to our first-generation, (super)stoichiometric protocol, this catalytic method enables faster and more efficient reactivity. Furthermore, lower oxidant concentration affords broader functional group tolerance, including alkenes, alkynes, alcohols, carbonyls, and heteroarenes. Mechanistic experiments interrogating the electronic nature of the key 1,5 H-atom transfer event are included, as well as probes for chemo-, regio-, and stereo-selectivity.
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Metrics
75
Total citations:
75
Citations from 2024:
11
(14%)
Cite this
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MLA
Cite this
GOST
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Stateman L. M. et al. Catalytic β C–H amination via an imidate radical relay // Chemical Science. 2019. Vol. 10. No. 9. pp. 2693-2699.
GOST all authors (up to 50)
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Stateman L. M., Wappes E. A., Nakafuku K. M., Edwards K. M., Nagib D. A. Catalytic β C–H amination via an imidate radical relay // Chemical Science. 2019. Vol. 10. No. 9. pp. 2693-2699.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/c8sc05685d
UR - https://xlink.rsc.org/?DOI=C8SC05685D
TI - Catalytic β C–H amination via an imidate radical relay
T2 - Chemical Science
AU - Stateman, Leah M
AU - Wappes, Ethan A.
AU - Nakafuku, Kohki M
AU - Edwards, Kara M
AU - Nagib, David A
PY - 2019
DA - 2019/01/17
PB - Royal Society of Chemistry (RSC)
SP - 2693-2699
IS - 9
VL - 10
PMID - 30996986
SN - 2041-6520
SN - 2041-6539
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Stateman,
author = {Leah M Stateman and Ethan A. Wappes and Kohki M Nakafuku and Kara M Edwards and David A Nagib},
title = {Catalytic β C–H amination via an imidate radical relay},
journal = {Chemical Science},
year = {2019},
volume = {10},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=C8SC05685D},
number = {9},
pages = {2693--2699},
doi = {10.1039/c8sc05685d}
}
Cite this
MLA
Copy
Stateman, Leah M., et al. “Catalytic β C–H amination via an imidate radical relay.” Chemical Science, vol. 10, no. 9, Jan. 2019, pp. 2693-2699. https://xlink.rsc.org/?DOI=C8SC05685D.