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      Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity

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          Abstract

          The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene.

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          Introduction of fluorine and fluorine-containing functional groups.

          Theresa Liang, Constanze N. Neumann, Tobias Ritter (2013)
          Over the past decade, the most significant, conceptual advances in the field of fluorination were enabled most prominently by organo- and transition-metal catalysis. The most challenging transformation remains the formation of the parent C-F bond, primarily as a consequence of the high hydration energy of fluoride, strong metal-fluorine bonds, and highly polarized bonds to fluorine. Most fluorination reactions still lack generality, predictability, and cost-efficiency. Despite all current limitations, modern fluorination methods have made fluorinated molecules more readily available than ever before and have begun to have an impact on research areas that do not require large amounts of material, such as drug discovery and positron emission tomography. This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
          Article 0 comments Cited 396 times – based on 0 reviews     Review now
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            Direct Trifluoromethylation of the CH Bond

            Hui Liu, Zhenhua Gu, Xuefeng Jiang (2013)
            Article 0 comments Cited 69 times – based on 0 reviews     Review now
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              Copper-mediated aerobic oxidative trifluoromethylation of terminal alkynes with Me3SiCF3.

              Feng-Ling Qing, Lingling Chu (2010)
              An efficient copper-mediated trifluoromethylation of terminal alkynes with nucleophilic trifluoromethylating reagent (Me(3)SiCF(3)) was developed. Both aromatic alkynes and aliphatic alkynes were effective, and a variety of functionalities such as amino, -OMe, -CO(2)Et, -Br, and -NO(2) were tolerated under the reaction conditions. This reaction provides a general, straightforward, and practically useful method to prepare trifluoromethylated acetylenes.
              Article 0 comments Cited 54 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 03 February 2014
                Publication date Collection: February 2014
                Volume: 19
                Issue: 2
                Pages: 1763-1774
                Affiliations
                [1 ]Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, Spain; E-Mails: nuria.aiguabella@ 123456irbbarcelona.org (N.A.); elsa_mtz@ 123456hotmail.es (E.M.A.); xavier.verdaguer@ 123456irbbarcelona.org (X.V.)
                [2 ]Department de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain; E-Mail: Carlos.Pozo@ 123456uv.es
                [3 ]Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, E-46012 Valencia, Spain
                [4 ]Department de Química Orgànica, Universitat de Barcelona, Martí i Franqués, 1. 08028 Barcelona, Spain
                Author notes
                [* ]Author to whom correspondence should be addressed; E-Mail: antoni.riera@ 123456irbbarcelona.org ; Tel.: +34-93-403-7093; Fax: +34-93-403-7095.
                Article
                Publisher ID: molecules-19-01763
                DOI: 10.3390/molecules19021763
                PMC ID: 6271263
                PubMed ID: 24496269
                SO-VID: ed38848e-86c1-480a-92d5-d6b674fddf61
                Copyright © © 2014 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 02 January 2014
                Date revision received : 15 January 2014
                Date accepted : 27 January 2014
                Categories
                Subject: Article

                Keywords: pauson-khand reaction,cycloadditions,regioselectivity,cyclopentenones,trifluoromethylalkynes
                Data availability:
                Keywords: pauson-khand reaction, cycloadditions, regioselectivity, cyclopentenones, trifluoromethylalkynes

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