Journal of Organic Chemistry, volume 88, issue 13, pages 9360-9371
Tandem C–H Annulation Reaction of Benzaldehydes and Aminobenzoic Acids with Two Equivalents of Alkyne toward Isocoumarin-Conjugated Isoquinolinium Salts: A Family of Organic Luminophores
Publication type: Journal Article
Publication date: 2023-06-16
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
A novel rhodium-catalyzed tandem C–H annulation of commercially available benzaldehydes and aminobenzoic acids with 2 equiv of alkyne is reported for the construction of isocoumarin-conjugated isoquinolinium salts that demonstrate diverse outstanding photoactivity. Depending on the substituents in the isoquinolinium moiety, they display either highly efficient fluorescence (up to 99% of quantum yield) or strong fluorescence quenching, which is provided by the transfer of the HOMO from the isoquinolinium to the isocoumarin moiety. Importantly, the functional groups in the benzaldehyde coupling partner also strongly affect the reaction selectivity, shifting the pathway to the formation of the photoinactive isocoumarin-substituted indenone imines and indenyl amines. Selective formation of the latter can be achieved by using a reduced amount of the oxidizing additive.
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Mendeleev Communications
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Mendeleev Communications
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Elsevier
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Elsevier
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Arsenov M. A. et al. Tandem C–H Annulation Reaction of Benzaldehydes and Aminobenzoic Acids with Two Equivalents of Alkyne toward Isocoumarin-Conjugated Isoquinolinium Salts: A Family of Organic Luminophores // Journal of Organic Chemistry. 2023. Vol. 88. No. 13. pp. 9360-9371.
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Arsenov M. A., Muratov D. V., Nelyubina Y. V., Loginov D. A. Tandem C–H Annulation Reaction of Benzaldehydes and Aminobenzoic Acids with Two Equivalents of Alkyne toward Isocoumarin-Conjugated Isoquinolinium Salts: A Family of Organic Luminophores // Journal of Organic Chemistry. 2023. Vol. 88. No. 13. pp. 9360-9371.
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TY - JOUR
DO - 10.1021/acs.joc.3c01008
UR - https://doi.org/10.1021%2Facs.joc.3c01008
TI - Tandem C–H Annulation Reaction of Benzaldehydes and Aminobenzoic Acids with Two Equivalents of Alkyne toward Isocoumarin-Conjugated Isoquinolinium Salts: A Family of Organic Luminophores
T2 - Journal of Organic Chemistry
AU - Arsenov, Mikhail A
AU - Muratov, Dmitry V.
AU - Nelyubina, Yulia V.
AU - Loginov, Dmitry A.
PY - 2023
DA - 2023/06/16 00:00:00
PB - American Chemical Society (ACS)
SP - 9360-9371
IS - 13
VL - 88
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2023_Arsenov,
author = {Mikhail A Arsenov and Dmitry V. Muratov and Yulia V. Nelyubina and Dmitry A. Loginov},
title = {Tandem C–H Annulation Reaction of Benzaldehydes and Aminobenzoic Acids with Two Equivalents of Alkyne toward Isocoumarin-Conjugated Isoquinolinium Salts: A Family of Organic Luminophores},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021%2Facs.joc.3c01008},
number = {13},
pages = {9360--9371},
doi = {10.1021/acs.joc.3c01008}
}
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Arsenov, Mikhail A., et al. “Tandem C–H Annulation Reaction of Benzaldehydes and Aminobenzoic Acids with Two Equivalents of Alkyne toward Isocoumarin-Conjugated Isoquinolinium Salts: A Family of Organic Luminophores.” Journal of Organic Chemistry, vol. 88, no. 13, Jun. 2023, pp. 9360-9371. https://doi.org/10.1021%2Facs.joc.3c01008.