Journal of the American Chemical Society, volume 138, issue 8, pages 2520-2523
Dual C–F, C–H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls
1
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078, United States
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Publication type: Journal Article
Publication date: 2016-02-18
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
PubMed ID:
26890498
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Multifluorinated biaryls are challenging to synthesize and yet are an important class of molecules. Because of the difficulty associated with selective fluorination, this class of molecules represent a formidable synthetic challenge. An alternative approach to selective fluorination of biaryls is to couple an arene that already possesses C-F bonds in the desired location. This strategy has been regularly utilized and relies heavily on traditional cross-coupling strategies that employ organometallics and halides (or pseudohalides) in order to achieve the coupling. Herein we report conditions for the photocatalytic coupling via direct functionalization of the C-F bond of a perfluoroarene and C-H bond of the other arene to provide an expedient route to multifluorinated biaryls. The mild conditions and good functional group tolerance enable a broad scope, including access to the anti-Minisci product of basic heterocycles. Finally, we demonstrate the value of the C-F functionalization approach by utilizing the high fluorine content to systematically build complex biaryls containing between two and five Caryl-F bonds via the synergistic use of photocatalysis and SNAr chemistry.
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Citations by publishers
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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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Senaweera S., Weaver J. D. Dual C–F, C–H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls // Journal of the American Chemical Society. 2016. Vol. 138. No. 8. pp. 2520-2523.
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Senaweera S., Weaver J. D. Dual C–F, C–H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls // Journal of the American Chemical Society. 2016. Vol. 138. No. 8. pp. 2520-2523.
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TY - JOUR
DO - 10.1021/jacs.5b13450
UR - https://doi.org/10.1021/jacs.5b13450
TI - Dual C–F, C–H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls
T2 - Journal of the American Chemical Society
AU - Senaweera, Sameera
AU - Weaver, Jimmie D
PY - 2016
DA - 2016/02/18 00:00:00
PB - American Chemical Society (ACS)
SP - 2520-2523
IS - 8
VL - 138
PMID - 26890498
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2016_Senaweera,
author = {Sameera Senaweera and Jimmie D Weaver},
title = {Dual C–F, C–H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls},
journal = {Journal of the American Chemical Society},
year = {2016},
volume = {138},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jacs.5b13450},
number = {8},
pages = {2520--2523},
doi = {10.1021/jacs.5b13450}
}
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Senaweera, Sameera, and Jimmie D Weaver. “Dual C–F, C–H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls.” Journal of the American Chemical Society, vol. 138, no. 8, Feb. 2016, pp. 2520-2523. https://doi.org/10.1021/jacs.5b13450.