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Palladium-catalyzed intramolecular aminofluorination of unactivated alkenes.
J Am Chem Soc. 2009 Nov 18; 131(45):16354-5.JA

Abstract

A novel palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes has been developed, in which AgF was used as a key fluorinating reagent and PhI(OPiv)(2) as oxidant. The reaction afforded vicinal fluoroamine products with very high regioselectivity. A Pd(II/IV) catalytic cycle was proposed, and preliminary mechanistic studies indicated that direct reductive elimination of Pd(IV) intermediates is favored, albeit competing with S(N)2 nucleophilic attack by fluorine, to form a C-F bond.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wu T
State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Road, Shanghai, China, 200032.
Yin G
No affiliation info available
Liu G
No affiliation info available

MeSH

AlkenesAminesCatalysisCyclizationMolecular StructureOrganoplatinum CompoundsPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19856929

Citation

Wu, Tao, et al. "Palladium-catalyzed Intramolecular Aminofluorination of Unactivated Alkenes." Journal of the American Chemical Society, vol. 131, no. 45, 2009, pp. 16354-5.
Wu T, Yin G, Liu G. Palladium-catalyzed intramolecular aminofluorination of unactivated alkenes. J Am Chem Soc. 2009;131(45):16354-5.
Wu, T., Yin, G., & Liu, G. (2009). Palladium-catalyzed intramolecular aminofluorination of unactivated alkenes. Journal of the American Chemical Society, 131(45), 16354-5. https://doi.org/10.1021/ja9076588
Wu T, Yin G, Liu G. Palladium-catalyzed Intramolecular Aminofluorination of Unactivated Alkenes. J Am Chem Soc. 2009 Nov 18;131(45):16354-5. PubMed PMID: 19856929.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed intramolecular aminofluorination of unactivated alkenes. AU - Wu,Tao, AU - Yin,Guoyin, AU - Liu,Guosheng, PY - 2009/10/28/entrez PY - 2009/10/28/pubmed PY - 2010/2/13/medline SP - 16354 EP - 5 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 131 IS - 45 N2 - A novel palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes has been developed, in which AgF was used as a key fluorinating reagent and PhI(OPiv)(2) as oxidant. The reaction afforded vicinal fluoroamine products with very high regioselectivity. A Pd(II/IV) catalytic cycle was proposed, and preliminary mechanistic studies indicated that direct reductive elimination of Pd(IV) intermediates is favored, albeit competing with S(N)2 nucleophilic attack by fluorine, to form a C-F bond. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/19856929/Palladium_catalyzed_intramolecular_aminofluorination_of_unactivated_alkenes_ L2 - https://doi.org/10.1021/ja9076588 DB - PRIME DP - Unbound Medicine ER -