Philippe Panchaud

Universität Bern, Bern, BE, Switzerland

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Publications (8)43.6 Total impact

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    ABSTRACT: The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO(2) (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.
    Journal of the American Chemical Society 11/2010; · 10.68 Impact Factor
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    ABSTRACT: A novel reaction for the introduction of an azide moiety by means of a mild radical process is currently under development. Sulfonyl azides are suitable azidating agents for nucleophilic radicals, such as secondary and tertiary alkyl radicals. More electrophilic radicals, such as enolate radicals, do not react with sulfonyl azides. This feature allowed the development of efficient intra- and intermolecular carboazidations of olefins. Due to the versatility of the azido group, this reaction has an important synthetic potential, as already demonstrated by the preparation of the core of several alkaloids, particularly those containing an amino-substituted quaternary carbon center, such as FR901483.
    Chemistry 09/2004; 10(15):3606-14. · 5.83 Impact Factor
  • Philippe Panchaud, Philippe Renaud
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    ABSTRACT: The radical carboazidation of alkenes has been achieved in water with triethylborane as initiator. This efficient process is complete in 1 h at room temperature in an open system. These new tin-free carboazidation conditions are environmentally friendly and allow running reactions with an excess of either the alkene or the radical precursor. They are also suitable for simple radical azidation of alkyl iodides as well as for more complex cascade reactions involving annulation processes.
    The Journal of Organic Chemistry 05/2004; 69(9):3205-7. · 4.56 Impact Factor
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    ABSTRACT: A procedure for one-pot intermolecular radical addition of 2-iodoesters to terminal alkenes followed by azidation of the radical adduct has been developed. This sequential reaction represents an alkene carboazidation process. Its efficacy is demonstrated by the two-step preparation of various lactams such as pyrrolidinones, pyrrolizidinones, and indolizidinones. An easy access to spirolactams bearing an amino-substituted quaternary carbon center is also described. These compounds are important building blocks for the synthesis of numerous alkaloids such as, for instance, FR901483.
    The Journal of Organic Chemistry 05/2004; 69(8):2755-9. · 4.56 Impact Factor
  • Philippe Panchaud, Philippe Renaud
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    ABSTRACT: The radical carboazidation of alkenes could be achieved in water using triethylborane as initiator. This efficient process is complete in one hour at room temperature in an open system. These new tin-free azidation and carboazidation conditions are environmentally friendly and enable reactions to be run with an excess of either the alkene or the radical precursor. Furthermore, 3-pyridinesulfonyl azide could be used in order to avoid tedious purifications, especially when the reaction product has a similar chromatographic behavior to benzenesulfonyl azide, our original azidation reagent.
    CHIMIA International Journal for Chemistry 03/2004; 58(4):232-233. · 1.09 Impact Factor
  • Philippe Panchaud, Philippe Renaud
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    ABSTRACT: Radical azidations and carboazidations have been achieved using 3-pyridinesulfonyl azide as azidating agent. Due to its base properties and its polarity, the excess of reagent is readily removed at the end of the reaction by filtration through silica gel or by extraction with either aqueous 1 M HCl or 1 M CuSO4. The use of this reagent greatly facilitates the tedious purifications of the final azides frequently encountered when reactions are run according to the original procedure involving benzenesulfonyl azide.
    Advanced Synthesis & Catalysis 01/2004; 346(8):925-928. · 5.54 Impact Factor
  • Philippe Renaud, Cyril Ollivier, Philippe Panchaud
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    ABSTRACT: For Abstract see ChemInform Abstract in Full Text.
    Angewandte Chemie International Edition 10/2002; 41(18):3460-2. · 11.34 Impact Factor
  • Cyril Ollivier, Philippe Panchaud, Philippe Renaud
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 01/2001; 2001(10):1573-1578.