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Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations: oxidative annulations of cyclopropyl-substituted alkynes.
Org Biomol Chem. 2013 Jan 07; 11(1):142-8.OB

Abstract

The chemical behavior of cyclopropyl-substituted alkynes has been probed using the reaction conditions of ruthenium-catalyzed oxidative C-H/O-H and C-H/N-H bond functionalizations. The oxidative annulations proceeded with complete conservation of all cyclopropane fragments and allowed for the one-step preparation of synthetically useful cyclopropyl-substituted isocoumarins and isoquinolones with high regioselectivities and chemical yields. The connectivities of the key heterocyclic products were unambiguously established by X-ray diffraction analysis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Deponti M
Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany.
Kozhushkov SI
No affiliation info available
Yufit DS
No affiliation info available
Ackermann L
No affiliation info available

MeSH

AlkynesCatalysisCyclopropanesIsocoumarinsIsoquinolinesModels, MolecularMolecular StructureOrganometallic CompoundsOxidation-ReductionRuthenium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23111695

Citation

Deponti, Monica, et al. "Ruthenium-catalyzed C-H/O-H and C-H/N-H Bond Functionalizations: Oxidative Annulations of Cyclopropyl-substituted Alkynes." Organic & Biomolecular Chemistry, vol. 11, no. 1, 2013, pp. 142-8.
Deponti M, Kozhushkov SI, Yufit DS, et al. Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations: oxidative annulations of cyclopropyl-substituted alkynes. Org Biomol Chem. 2013;11(1):142-8.
Deponti, M., Kozhushkov, S. I., Yufit, D. S., & Ackermann, L. (2013). Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations: oxidative annulations of cyclopropyl-substituted alkynes. Organic & Biomolecular Chemistry, 11(1), 142-8. https://doi.org/10.1039/c2ob26250a
Deponti M, et al. Ruthenium-catalyzed C-H/O-H and C-H/N-H Bond Functionalizations: Oxidative Annulations of Cyclopropyl-substituted Alkynes. Org Biomol Chem. 2013 Jan 7;11(1):142-8. PubMed PMID: 23111695.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functionalizations: oxidative annulations of cyclopropyl-substituted alkynes. AU - Deponti,Monica, AU - Kozhushkov,Sergei I, AU - Yufit,Dmitry S, AU - Ackermann,Lutz, PY - 2012/11/1/entrez PY - 2012/11/1/pubmed PY - 2013/5/17/medline SP - 142 EP - 8 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 11 IS - 1 N2 - The chemical behavior of cyclopropyl-substituted alkynes has been probed using the reaction conditions of ruthenium-catalyzed oxidative C-H/O-H and C-H/N-H bond functionalizations. The oxidative annulations proceeded with complete conservation of all cyclopropane fragments and allowed for the one-step preparation of synthetically useful cyclopropyl-substituted isocoumarins and isoquinolones with high regioselectivities and chemical yields. The connectivities of the key heterocyclic products were unambiguously established by X-ray diffraction analysis. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/23111695/Ruthenium_catalyzed_C_H/O_H_and_C_H/N_H_bond_functionalizations:_oxidative_annulations_of_cyclopropyl_substituted_alkynes_ DB - PRIME DP - Unbound Medicine ER -