Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
J Am Chem Soc. 2010 Dec 15;132(49):17511-5. doi: 10.1021/ja1068036. Epub 2010 Nov 17.
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 SO2 (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.
本文报道了利用亲电性的烷磺酰基叠氮化物引发的末端烯烃的自由基碳氮键加成反应。该反应使用单一组分试剂提供了所需的亲电烷基自由基和叠氮基团，并且通过使用中等过量的碳氮键加成试剂（1.5-2 当量）可以获得良好的收率。有趣的是，除了起始的磺酰叠氮化物外，该方法仅需要使用自由基引发剂，二特丁基二氮烯。从原子经济性的角度来看，这个叠氮转移反应非常理想，因为 SO2（1 当量）是唯一的副产物。该过程的合成潜力已通过生物碱 Lepadiformine C 的形式合成得到证明。
