Aldehydes as photoremovable directing groups: synthesis of pyrazoles by a photocatalyzed [3+2] cycloaddition/norrish type fragmentation sequence
Entity
UAM. Departamento de Química OrgánicaPublisher
American Chemical SocietyDate
2021-06-07Citation
10.1021/acs.orglett.1c01665
Organics Letters 23.12 (2021): 4903-4908
ISSN
1523-7060; 1523-7052 (online)DOI
10.1021/acs.orglett.1c01665Funded by
This work was supported by the MINECO (CTQ2014-53894-R and CTQ2017-85454-C2-2-P) and FEDER/MICIU (PGC2018-098660-B-I00) of Spain. L.O.-R. thanks MINECO for a FPI fellowship, and A.P.-E. thanks CAM for a postdoctoral fellowshipProject
Gobierno de España. CTQ2014-53894-R; Gobierno de España. CTQ2017-85454-C2-2-PEditor's Version
https://doi.org/10.1021/acs.orglett.1c01665Subjects
Cyclooctanes; Peracetylated N-Azidoacetylmannosamine; Click Chemistry; QuímicaRights
© 2021 American Chemical SocietyAbstract
A straightforward methodology for the regioselective synthesis of pyrazoles has been developed by a domino sequence based on a photoclick cycloaddition followed by a photocatalyzed oxidative deformylation reaction. Distinguishing features of this protocol include an unprecedented photoredox-catalyzed Norrish type fragmentation under green-light irradiation and the use of α,β-unsaturated aldehydes as synthetic equivalents of alkynes, where the aldehyde is acting as a novel photoremovable directing group
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Google Scholar:Pascual-Escudero, Ana
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Ortiz-Rojano, Laura
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Simón-Fuente, Silvia
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Adrio Sevilla, Francisco Javier
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Ribagorda Lobera, María
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