Cooperative photoredox/gold catalysed cyclization of 2-alkynylbenzoates with arenediazonium salts: synthesis of 3,4-disubstituted isocoumarins
Publication type: Journal Article
Publication date: 2022-09-29
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
36200334
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Several isocoumarins have been synthesised in good to excellent yields starting from 2-alkynylbenzoates and arenediazonium salts. The strategy involves a domino arylation/oxo-cyclization catalysed by a dual photoredox/gold catalytic system. The reactions run under mild conditions at room temperature in wet acetonitrile under irradiation with a blue-LED lamp, in the presence of a cationic gold catalyst and a cheap organic photocatalyst. The scope is quite broad and allows the preparation of isocoumarins differently disubstituted in positions 3 and 4. A plausible reaction mechanism is proposed.
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Pirovano V. et al. Cooperative photoredox/gold catalysed cyclization of 2-alkynylbenzoates with arenediazonium salts: synthesis of 3,4-disubstituted isocoumarins // Organic and Biomolecular Chemistry. 2022. Vol. 20. No. 41. pp. 8065-8070.
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Pirovano V., Brambilla E., Fanciullacci G., Abbiati G. Cooperative photoredox/gold catalysed cyclization of 2-alkynylbenzoates with arenediazonium salts: synthesis of 3,4-disubstituted isocoumarins // Organic and Biomolecular Chemistry. 2022. Vol. 20. No. 41. pp. 8065-8070.
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TY - JOUR
DO - 10.1039/d2ob01371a
UR - https://xlink.rsc.org/?DOI=D2OB01371A
TI - Cooperative photoredox/gold catalysed cyclization of 2-alkynylbenzoates with arenediazonium salts: synthesis of 3,4-disubstituted isocoumarins
T2 - Organic and Biomolecular Chemistry
AU - Pirovano, Valentina
AU - Brambilla, Elisa
AU - Fanciullacci, Giorgia
AU - Abbiati, Giorgio
PY - 2022
DA - 2022/09/29
PB - Royal Society of Chemistry (RSC)
SP - 8065-8070
IS - 41
VL - 20
PMID - 36200334
SN - 1477-0520
SN - 1477-0539
ER -
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@article{2022_Pirovano,
author = {Valentina Pirovano and Elisa Brambilla and Giorgia Fanciullacci and Giorgio Abbiati},
title = {Cooperative photoredox/gold catalysed cyclization of 2-alkynylbenzoates with arenediazonium salts: synthesis of 3,4-disubstituted isocoumarins},
journal = {Organic and Biomolecular Chemistry},
year = {2022},
volume = {20},
publisher = {Royal Society of Chemistry (RSC)},
month = {sep},
url = {https://xlink.rsc.org/?DOI=D2OB01371A},
number = {41},
pages = {8065--8070},
doi = {10.1039/d2ob01371a}
}
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Pirovano, Valentina, et al. “Cooperative photoredox/gold catalysed cyclization of 2-alkynylbenzoates with arenediazonium salts: synthesis of 3,4-disubstituted isocoumarins.” Organic and Biomolecular Chemistry, vol. 20, no. 41, Sep. 2022, pp. 8065-8070. https://xlink.rsc.org/?DOI=D2OB01371A.