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Regio- and Stereoselective Allylic Trifluoromethylation and Fluorination using CuCF3 and CuF Reagents.
2013 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 78, no 14, p. 7330-7336Article in journal (Refereed) Published
Abstract [en]

Copper-mediated trifluoromethylation of allylic chlorides and trifluoroacetates was performed using a convenient Cu-CF3 reagent. The reaction is suitable for selective synthesis of allyl trifluoromethyl species. Mechanistic studies indicate that the reaction proceeds via a nucleophilic substitution mechanism involving allyl copper intermediates. The analogous Cu-F reagent was suitable for fluorination of allyl chlorides. Stereodefined cyclic substrates reacted regio- and stereoselectively. [on SciFinder(R)]

Place, publisher, year, edition, pages
American Chemical Society , 2013. Vol. 78, no 14, p. 7330-7336
Keywords [en]
allylic chloride trifluoroacetate trifluoromethylation fluorination regioselective stereoselective, trifluoromethyl fluoro copper reagent allylic substitution
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-374751DOI: 10.1021/jo4010074OAI: oai:DiVA.org:uu-374751DiVA, id: diva2:1282031
Note

Copyright (C) 2019 American Chemical Society (ACS). All Rights Reserved.; CAPLUS AN 2013:982546(Journal; Online Computer File)

Available from: 2019-01-23 Created: 2019-01-23 Last updated: 2019-01-23

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Larsson, Johanna M.
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