Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science & Technology (KAIST), Daejeon 305-701, Korea.
Chem Asian J. 2011 Oct 4;6(10):2618-34. doi: 10.1002/asia.201100340. Epub 2011 Jul 11.
Whereas alkyl and aryl azides readily react with terminal alkynes to afford 1,4-disubstituted-1,2,3-triazoles in excellent yields and selectivity in the presence of a copper catalyst, sulfonyl, phosphoryl, and certain acyl azides allow additional chemistry upon ring-opening of the corresponding copper-triazole intermediates. The amazingly versatile new chemistry stems from the high reactivity of a ring-opened ketenimine intermediate, with which a wide range of nucleophiles react to give multicomponent products. Among those nucleophiles, amines, alcohols, water, and heterocyclic compounds are especially capable of being involved in this new chemistry.
虽然烷基和芳基叠氮化物在铜催化剂的存在下容易与末端炔烃反应，以极好的收率和选择性得到 1,4-二取代-1,2,3-三唑，但磺酰基、膦基和某些酰基叠氮化物允许在相应的铜-三唑中间体开环后进行额外的化学反应。这种令人惊讶的多功能新化学源于开环的酮亚胺中间体的高反应性，其中各种亲核试剂与之反应生成多组分产物。在这些亲核试剂中，胺、醇、水和杂环化合物特别能够参与这种新的化学。
