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Copper-Catalyzed Ring-Opening 1,3-Aminotrifluoromethylation of Arylcyclopropanes.

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The copper-catalyzed reaction of arylcyclopropanes, N-fluorobis(arenesulfonyl)imides, and (bpy)Zn(CF3)2 (bpy = 2,2'-bipyridine) at room temperature affords the corresponding ring-opening 1,3-aminotrifluoromethylation products in satisfactory yields. The protocol is highly regioselective, providing a… Click to show full abstract

The copper-catalyzed reaction of arylcyclopropanes, N-fluorobis(arenesulfonyl)imides, and (bpy)Zn(CF3)2 (bpy = 2,2'-bipyridine) at room temperature affords the corresponding ring-opening 1,3-aminotrifluoromethylation products in satisfactory yields. The protocol is highly regioselective, providing a convenient entry to γ-trifluoromethylated amines. A mechanism involving the trifluoromethylation of benzyl radicals is proposed.

Keywords: ring opening; aminotrifluoromethylation arylcyclopropanes; opening aminotrifluoromethylation; catalyzed ring; copper catalyzed

Journal Title: Organic letters
Year Published: 2021

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