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Catalysis of Diazoalkane–Carbonyl Homologation. How New Developments in Hydrazone Oxidation Enable the Carbon Insertion Strategy for Synthesis

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C-C Bond Activation

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 346))

Abstract

Diazo compounds continue both to challenge and to fascinate practitioners of chemical synthesis. The most strategically powerful and unique type of reactivity observed with these reagents is a formal insertion of the donor-acceptor carbon into C–C or C–H bonds alpha to carbonyl groups. Although the reaction does not involve discrete carbon–metal bonds, it can be catalyzed by metal-based Lewis acids. This chapter investigates both classical and modern developments in diazoalkyl carbon insertion with a special emphasis on nonstabilized nucleophiles.

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Notes

  1. 1.

    Interestingly, Tiffeneau–Demjanov rearrangement provides mostly the α-ketone product in an 85:15 ratio of regioisomers (determined by IR spectroscopy); see [83])

    figure a
  2. 2.

    See [90].

    figure b
  3. 3.

    See [102].

    figure c
  4. 4.

    Readily prepared by treating trimethylaluminum with two equivalents of BHT; see [99].

  5. 5.

    The cis/trans configuration of 2-methyl-5-tert-butylcycloheptanone was established following equilibration in methanolic NaOCH3.

  6. 6.

    The less electron-poor, more hindered Lewis acids (Sc(acac)3 and Sc(tmhd)3) were substituted for Sc(OTf)3 in reactions with more Lewis basic diazoalkanes in order to maximize the yield of product (tmhd = 2,2,6,6-tetramethyl-3,5-heptanedianato, or tert-butyl(acac)). See [99] and citations therein for more details on the Lewis-acid mediated destruction of diazoalkanes.

  7. 7.

    p-(Methoxy)phenyldiazomethane is a potent Lewis base and has been reported to decompose at temperatures as low as –80° C; see [125].

  8. 8.

    Yields in Fig. 4 were determined by manometric titration, as described in [51].

  9. 9.

    Iodobenzene bis(trifluoroacetate) can substitute for lead(IV) acetate with little or no impact on the yield of diazoalkane, but the nonpolar extract becomes contaminated by residual iodobenzene.

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  1. Onyx Pharmaceuticals, Inc., 249 E. Grand Avenue, South San Francisco, CA, 94080, USA

    David C. Moebius

  2. Pharmaceutical Sciences, Massachusetts College of Pharmacy and Health Sciences, 179 Longwood Avenue, Boston, MA, 02115, USA

    Victor L. Rendina (Assistant Professor)

  3. Chemistry, California Lutheran University, 60 West Olsen Road, #3700, Thousand Oaks, CA, 91360, USA

    Jason S. Kingsbury (Assistant Professor)

Authors
  1. David C. Moebius
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  2. Victor L. Rendina
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  3. Jason S. Kingsbury
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Correspondence to Jason S. Kingsbury .

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  1. The University of Texas at Austin Department of Chemistry & Biochemistry, Austin, USA

    Guangbin Dong

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© 2014 Springer-Verlag Berlin Heidelberg

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Moebius, D.C., Rendina, V.L., Kingsbury, J.S. (2014). Catalysis of Diazoalkane–Carbonyl Homologation. How New Developments in Hydrazone Oxidation Enable the Carbon Insertion Strategy for Synthesis. In: Dong, G. (eds) C-C Bond Activation. Topics in Current Chemistry, vol 346. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_521

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