Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 27, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202200272
Keywords
hypervalent iodine; azide; alcohol; late-stage functionalization; click reaction
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Funding
- National Natural Science Foundation of China [22071116, 21772096]
- National Key Research and Development Program of China [2017YFD020030202]
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A practical method for dehydroxyazidation of alcohols using PPh3 and hypervalent azido-iodine(III) reagents is reported. The method allows for the late-stage azidation of structurally complex alcohols and the synthesis of the antiepileptic drug rufinamide.
The development of convenient new methods for the synthesis of organic azides is highly desirable. Herein, we report a practical method for dehydroxyazidation of alcohols via an S(N)2 pathway involving PPh3 and trifunctional benziodazolone-based hypervalent azido-iodine(III) reagents, which function as an electrophilic center, an azido source, and a base. This mild, chemoselective method was used for late-stage azidation of structurally complex alcohols, as well as for a new synthetic route to the antiepileptic drug rufinamide. The reaction mechanism was also investigated both experimentally and computationally.
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