Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY
Publication type: Journal Article
Publication date: 2015-07-28
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
26186141
Organic Chemistry
Abstract
An effective, stepwise methodology for polychlorination of BODIPY using trichloroisocyanuric acid (TCCA) in acetic acid was developed. In this way, selectively substituted di-, tri-, tetra-, and pentachloro-BODIPYs 2-5 were prepared. The pentachloro-BODIPY is shown to undergo regioselective Pd(0)-catalyzed Stille and Suzuki coupling reactions, first at the 8-position followed by the 3,5- and then the 2,6-positions; nucleophilic substitution reactions occur first at the 8- followed by the 3,5-positions, while the 2,6 are unreactive.
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56
Total citations:
56
Citations from 2024:
7
(12.5%)
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Zhao N. et al. Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY // Journal of Organic Chemistry. 2015. Vol. 80. No. 16. pp. 8377-8383.
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Zhao N., Xuan S., Fronczek F., Smith K. S., Vicente M. A. Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY // Journal of Organic Chemistry. 2015. Vol. 80. No. 16. pp. 8377-8383.
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TY - JOUR
DO - 10.1021/acs.joc.5b01147
UR - https://doi.org/10.1021/acs.joc.5b01147
TI - Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY
T2 - Journal of Organic Chemistry
AU - Zhao, Ning
AU - Xuan, Sunting
AU - Fronczek, Frank
AU - Smith, Kevin S.
AU - Vicente, M. A.
PY - 2015
DA - 2015/07/28
PB - American Chemical Society (ACS)
SP - 8377-8383
IS - 16
VL - 80
PMID - 26186141
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2015_Zhao,
author = {Ning Zhao and Sunting Xuan and Frank Fronczek and Kevin S. Smith and M. A. Vicente},
title = {Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY},
journal = {Journal of Organic Chemistry},
year = {2015},
volume = {80},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.5b01147},
number = {16},
pages = {8377--8383},
doi = {10.1021/acs.joc.5b01147}
}
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Zhao, Ning, et al. “Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.” Journal of Organic Chemistry, vol. 80, no. 16, Jul. 2015, pp. 8377-8383. https://doi.org/10.1021/acs.joc.5b01147.