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Pd(II)-Catalyzed Allylic C–H Amination for the Preparation of 1,2- and 1,3-Cyclic Ureas

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posted on 2015-02-20, 00:00 authored by Yasuhiro Nishikawa, Seikou Kimura, Yuri Kato, Natsuka Yamazaki, Osamu Hara
A general synthesis of 1,2- and 1,3-cyclic ureas is accomplished by intramolecular allylic C–H amination employing Pd­(TFA)2/bis-sulfoxide as a catalyst. By careful modification of substrates and catalyst, a variety of 1,2-cyclic ureas are accessible from not previously employed terminal olefins substituted in allylic or vinylic positions. Furthermore, MS4A is found to be an effective additive for the synthesis of 1,3-cyclic ureas in good yields and excellent diastereoselectivities.

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