Visible-Light-Induced Regioselective C–H Sulfenylation of Pyrazolo[1,5-a]pyrimidines via Cross-Dehydrogenative Coupling
Тип публикации: Journal Article
Дата публикации: 2023-03-14
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
36916032
Organic Chemistry
Краткое описание
A visible-light-induced cross-dehydrogenative methodology has been developed for the regioselective sulfenylation of pyrazolo[1,5-a]pyrimidine derivatives. Rose bengal, blue LEDs, KI, K2S2O8, and DMSO are all essential for this photocatalytic transformation. The protocol is applicable for the synthesis of a library of 3-(aryl/heteroaryl thio)pyrazolo[1,5-a]pyrimidine derivatives with broad functionalities. The selectivity and scalability of the methodology have been also demonstrated. Moreover, the efficiency of this strategy for sulfenylation of pyrazoles, indole, imidazoheterocycles, and 4-hydroxy coumarin has been proven. The mechanistic investigation revealed the radical-based mechanism and formation of diaryl disulfide as a key intermediate for this cross-dehydrogenative coupling reaction.
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Paul S. et al. Visible-Light-Induced Regioselective C–H Sulfenylation of Pyrazolo[1,5-a]pyrimidines via Cross-Dehydrogenative Coupling // Journal of Organic Chemistry. 2023. Vol. 88. No. 7. pp. 4187-4198.
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Paul S., Das S., Choudhuri T., Sikdar P., Bagdi A. K. Visible-Light-Induced Regioselective C–H Sulfenylation of Pyrazolo[1,5-a]pyrimidines via Cross-Dehydrogenative Coupling // Journal of Organic Chemistry. 2023. Vol. 88. No. 7. pp. 4187-4198.
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TY - JOUR
DO - 10.1021/acs.joc.2c02665
UR - https://pubs.acs.org/doi/10.1021/acs.joc.2c02665
TI - Visible-Light-Induced Regioselective C–H Sulfenylation of Pyrazolo[1,5-a]pyrimidines via Cross-Dehydrogenative Coupling
T2 - Journal of Organic Chemistry
AU - Paul, Suvam
AU - Das, Sourav
AU - Choudhuri, Tathagata
AU - Sikdar, Papiya
AU - Bagdi, Avik Kumar
PY - 2023
DA - 2023/03/14
PB - American Chemical Society (ACS)
SP - 4187-4198
IS - 7
VL - 88
PMID - 36916032
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2023_Paul,
author = {Suvam Paul and Sourav Das and Tathagata Choudhuri and Papiya Sikdar and Avik Kumar Bagdi},
title = {Visible-Light-Induced Regioselective C–H Sulfenylation of Pyrazolo[1,5-a]pyrimidines via Cross-Dehydrogenative Coupling},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.2c02665},
number = {7},
pages = {4187--4198},
doi = {10.1021/acs.joc.2c02665}
}
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MLA
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Paul, Suvam, et al. “Visible-Light-Induced Regioselective C–H Sulfenylation of Pyrazolo[1,5-a]pyrimidines via Cross-Dehydrogenative Coupling.” Journal of Organic Chemistry, vol. 88, no. 7, Mar. 2023, pp. 4187-4198. https://pubs.acs.org/doi/10.1021/acs.joc.2c02665.