Elsevier

Tetrahedron Letters

Volume 51, Issue 8, 24 February 2010, Pages 1172-1175
Tetrahedron Letters

Catalytic alkylation of benzylic C–H bonds with 1,3-dicarbonyl compounds utilizing oxygen as terminal oxidant

https://doi.org/10.1016/j.tetlet.2009.12.080Get rights and content

Abstract

The oxidative alkylation of benzylic C–H bonds with 1,3-dicarbonyl compounds was developed using oxygen as the terminal oxidant in the presence of catalytic amounts of FeCl2, CuCl and NHPI.

Section snippets

Acknowledgments

We thank the Canada Research Chair (Tier 1) foundation (to CJL) and NSERC for their support to this research. C.A.C. would also like to thank McGill University for post-graduate fellowships (Bill and Christina Chan Fellowship and Principle’s Graduate Fellowship).

References and notes (14)

  • R.G. Bergman

    Nature

    (2007)
    C. Jia et al.

    Acc. Chem. Res.

    (2001)
    V. Ritleng et al.

    Chem. Rev.

    (2002)
    G. Dyker

    Handbook of C–H Transformations

    (2005)
    K. Godula et al.

    Science

    (2006)
    J.-Q. Yu et al.

    Org. Biomol. Chem.

    (2006)
    D. Alberico et al.

    Chem. Rev.

    (2007)
    C. Herrerias et al.

    Chem. Rev.

    (2007)
    C.-J. Li

    Acc. Chem. Res.

    (2009)
  • T. Watanabe et al.

    Org. Lett.

    (2008)
    C. Zhang et al.

    Dalton Trans.

    (2009)
    K. Xu et al.

    Organometallics

    (2009)
    L. Zhao et al.

    PNAS

    (2009)
    Z. Li et al.

    J. Am. Chem. Soc.

    (2006)
    C.-J. Li et al.

    Pure Appl. Chem.

    (2006)
    Y. Zhang et al.

    J. Am. Chem. Soc.

    (2006)
    G. Deng et al.

    Adv. Synth. Catal.

    (2009)
    G. Deng et al.

    Org. Lett.

    (2009)
    G. Deng et al.

    Angew. Chem., Int. Ed.

    (2008)
    S.-Y. Zhang et al.

    Chem. Eur. J.

    (2008)
    S.J. Pastine et al.

    J. Am. Chem. Soc.

    (2006)
    L. Shi et al.

    J. Am. Chem. Soc.

    (2005)
  • M. Yasuda et al.

    Angew. Chem., Int. Ed.

    (2006)
    J. Kischel et al.

    Adv. Synth. Catal.

    (2007)
    S.A. Babu et al.

    Synthesis

    (2008)
    Y. Yuan et al.

    Appl. Organomet. Chem.

    (2007)
    U. Jana et al.

    Tetrahedron Lett.

    (2007)
  • R. Sanz et al.

    Org. Lett.

    (2007)
    J.S. Yadav et al.

    Tetrahedron Lett.

    (2008)
  • Z. Li et al.

    Angew. Chem., Int. Ed.

    (2007)
    N. Borduas et al.

    J. Org. Chem.

    (2008)
  • S.-I. Murahashi et al.

    J. Am. Chem. Soc.

    (2003)
    O. Basle et al.

    Green Chem.

    (2007)
    O. Basle et al.

    Org. Lett.

    (2008)
    S.-I. Murahashi et al.

    J. Am. Chem. Soc.

    (2008)
    Y. Shen et al.

    Chem. Commun.

    (2009)
    S. Singhal et al.

    Chem. Commun.

    (2009)
There are more references available in the full text version of this article.

Cited by (41)

  • Recent strategic advances for the activation of benzylic C–H bonds for the formation of C–C bonds

    2019, Tetrahedron Letters
    Citation Excerpt :

    The formed radical cation intermediate underwent the intramolecular SET process. The authors moreover expanded the substrate scope by changing the nickel catalyst to manganese- and cobalt-based catalysts (Scheme 18) [23]. Thus, various α-tertiary β-arylethylamines can be synthesized using alkylarenes as alkylating reagents.

  • Kharasch reaction: Cu-catalyzed and non-Kharasch metal-free peroxidation of barbituric acids

    2019, Tetrahedron Letters
    Citation Excerpt :

    It should be noted that the reactions of unsubstituted barbituric acids 3a-c proceed only in the presence of copper(II) tetrafluoroborate hexahydrate as the catalyst. Taking into account the published data [98–102], it can be suggested that the peroxidation of α-substituted barbituric acids 1a-u occurs according to Scheme 3. Initially, Cu(II) oxidizes ButOOH to the ButOO radical to form monovalent copper (step I) [65,84,103].

  • Air-stable μ<sup>2</sup>-hydroxyl bridged cationic binuclear complexes of zirconocene perfluorooctanesulfonates: their structures, characterization and application

    2018, Tetrahedron
    Citation Excerpt :

    However, 2-naphthaldehyde with large steric hindrance was tolerated in this process, providing compound 5o in 55% and 50% yields over 2a·6H2O and 3a·2C3H6O·8H2O, respectively (entry 6). Finally, the catalytic activities of 1a·2THF·4H2O and 2a·6H2O together with 3a·2C3H6O·8H2O were evaluated for the classical Friedel-Crafts acylation of aromatic compounds.56 The reactions proceed well in the presence of traditional Lewis acids such as ZnCl2, AlCl3, FeCl3, SnCl4, and TiCl457 or strong protic acids (e.g., HF, CF3SO3H or H2SO4).58

  • Synthesis and structure of an air-stable bis(isopropylcyclopentadienyl) zirconium perfluorooctanesulfonate and its catalyzed benzylation of 1,3-dicarbonyl derivatives with alcohols

    2015, Tetrahedron
    Citation Excerpt :

    Therefore, it is highly desirable to develop an environmental friendly and atom-economical process to improve this transformation. Among the numerous works devoted to this alkylation of 1,3-dicarbonyl compounds,3 the most ideal protocol would be the use of alcohols as the alkylating agents,4 wherein alcohols can be obtained more easily and H2O is the only side product (Scheme 1). Very recently, various catalytic systems have been successfully applied in the direct alkylation of active methylenes using alcohols as electrophiles.

View all citing articles on Scopus
View full text