铜催化的烯烃分子间氨基叠氮化反应。

Copper-catalyzed intermolecular aminoazidation of alkenes.

机构信息

Institute of Organic Chemistry, Westfälische Wilhems-University , Corrensstraße 40, 48149 Münster, Germany.

出版信息

Org Lett. 2014 Mar 21;16(6):1790-3. doi: 10.1021/ol500513b. Epub 2014 Mar 3.

Abstract

Copper-catalyzed intermolecular aminoazidation of alkenes is described. This novel methodology provides an efficient approach to vicinal amino azides which can easily be transformed into other valuable amine derivatives. The commercially available N-fluorobenzenesulfonimide (NFSI) is used as a nitrogen-radical precursor and TMSN3 as the N3 source. Yields are moderate to excellent, and for internal alkenes aminoazidation occurs with excellent diastereoselectivity.

摘要

铜催化的烯烃分子间氨基叠氮化反应被描述。这种新方法为顺式氨基叠氮化物提供了一种有效的途径，而顺式氨基叠氮化物可以很容易地转化为其他有价值的胺衍生物。商业上可用的 N-氟代苯磺酰亚胺（NFSI）用作氮自由基前体，TMSN3 用作 N3 源。产率中等至优秀，对于内部烯烃，氨基叠氮化反应具有极好的非对映选择性。