Tetrahedron

Formation of benzylamines from triazene compounds via a 1, 2-proton shift

K Nishiwaki, T Ogawa, K Shigeta, K Takahashi…

Index: Nishiwaki, Keiji; Ogawa, Takashi; Shigeta, Kazumi; Takahashi, Koichi; Matsuo, Keizo Tetrahedron, 2006 , vol. 62, # 29 p. 7034 - 7042

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Citation Number: 12

Abstract

A new approach to benzylamines using triazene compounds has been developed that is facilitated by the lithiation of aryltriazenes followed by treatment with an electrophile. The regioselectivity of the reaction can be controlled by means of the substituents in the aryl group. The reaction contains the following steps: intramolecular carbon–carbon bond formation involving lithiation of an alkyl group on a 3-nitrogen atom; a 1, 2-proton shift; and ...