Journal of the American Chemical Society, volume 139, issue 33, pages 11527-11536
Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
Publication type: Journal Article
Publication date: 2017-08-08
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
PubMed ID:
28735532
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C–H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.
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Citations by publishers
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5
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American Chemical Society (ACS)
29 publications, 30.21%
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Wiley
24 publications, 25%
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The Royal Society
1 publication, 1.04%
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Multidisciplinary Digital Publishing Institute (MDPI)
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King Saud University
1 publication, 1.04%
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Taylor & Francis
1 publication, 1.04%
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1 publication, 1.04%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 1.04%
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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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Perry G. J. P. et al. Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings // Journal of the American Chemical Society. 2017. Vol. 139. No. 33. pp. 11527-11536.
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Perry G. J. P., Quibell J. M., Panigrahi A., Larrosa I. Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings // Journal of the American Chemical Society. 2017. Vol. 139. No. 33. pp. 11527-11536.
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TY - JOUR
DO - 10.1021/jacs.7b05155
UR - https://doi.org/10.1021/jacs.7b05155
TI - Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
T2 - Journal of the American Chemical Society
AU - Panigrahi, Adyasha
AU - Larrosa, Igor
AU - Perry, Gregory J. P.
AU - Quibell, Jacob M
PY - 2017
DA - 2017/08/08 00:00:00
PB - American Chemical Society (ACS)
SP - 11527-11536
IS - 33
VL - 139
PMID - 28735532
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2017_Perry,
author = {Adyasha Panigrahi and Igor Larrosa and Gregory J. P. Perry and Jacob M Quibell},
title = {Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings},
journal = {Journal of the American Chemical Society},
year = {2017},
volume = {139},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/jacs.7b05155},
number = {33},
pages = {11527--11536},
doi = {10.1021/jacs.7b05155}
}
Cite this
MLA
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Perry, Gregory J. P., et al. “Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.” Journal of the American Chemical Society, vol. 139, no. 33, Aug. 2017, pp. 11527-11536. https://doi.org/10.1021/jacs.7b05155.