Tetrahedron

Synthetic and mechanistic aspects of cross-coupling of nitroxyl radicals of 3-imidazoline series with terminal alkynes

SF Vasilevsky, OL Krivenko, VR Gorelik, IV Alabugin

Index: Vasilevsky, Sergei F.; Krivenko, Olga L.; Gorelik, Vitalii R.; Alabugin, Igor V. Tetrahedron, 2008 , vol. 64, # 37 p. 8807 - 8814

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Citation Number: 4

Abstract

Practical synthetic approaches to the new class of acetylenic derivatives of 3-imidazolyl-3- oxide-1-oxyls, including biradicals, were developed through cross-coupling reactions of 3- imidazolyl halides with either terminal alkynes or their copper salts. The presence of nitroxyl functional group as an internal oxidant leads to a competition between the formation of cross- coupling products and the products of oxidative homocoupling. The balance in this ...