Palladium-catalyzed ortho-olefination of 2-arylpyrrolidines: A tool for increasing structural complexity in nitrogen heterocycles
Entity
UAM. Departamento de Química OrgánicaPublisher
ElsevierDate
2018-07-19Citation
10.1016/j.tet.2018.05.076
Tetrahedron 74.29 (2018): 3947-3954
ISSN
0040-4020DOI
10.1016/j.tet.2018.05.076Funded by
We thank the Spanish Ministerio de Economía y Competitividad (MINECO, Project CTQ2012-35790), and MINECO/FEDER, UE (Project CTQ2015-66954-P) for financial support. P.D.L. thanks MECD for a FPU predoctoral fellowshipProject
Gobierno de España. CTQ2012-35790; Gobierno de España. CTQ2015-66954-PEditor's Version
https://doi.org/10.1016/j.tet.2018.05.076Subjects
Benzazepinone; Benzopyrrolizidine; C–H alkenylation; Heterocycles; Palladium; Pyridine directing group; Pyrrolidine; QuímicaNote
This Accepted Manuscript is available for reuse under a CC BY-NC-ND licence after the 24 month embargo period provided that all the terms of the licence are adhered toRights
© 2018 Elsevier LtdEsta obra está bajo una licencia de Creative Commons Reconocimiento-NoComercial-SinObraDerivada 4.0 Internacional.
Abstract
The dual role of the (2-pyridyl)sulfonyl unit as directing functionality and readily removable N-protecting group has enabled an efficient and practical transformation of 2-arylpyrrolidine derivatives into more complex tricyclic frameworks via palladium-catalyzed ortho-olefination with electron deficient alkenes and subsequent cyclization upon N-deprotection under mild conditions. The key cross coupling step in the presence of N-fluoro-2,4,6-trimethylpyridinium triflate ([F+]) as the terminal oxidant is both highly efficient and tolerant to a variety of steric and electronic changes at both coupling partners. By adequate choice of reductive conditions, the N-sulfonyl deprotection can be directed to the selective formation of benzo-fused pyrrolizidine or fused pyrrolidino-benzazapine frameworks.
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Google Scholar:Legarda, Pablo D.
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García-Rubia, Alfonso
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Arrayás, Ramón Gómez
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Carretero Gonzálvez, Juan Carlos
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