Formation of benzylamines from triazene compounds via a 1,2-proton shift |
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Authors: | Keiji Nishiwaki Takashi Ogawa Koichi Takahashi |
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Affiliation: | a Department of Pharmaceutical Sciences, School of Pharmacy, Kinki University, 3-4-1 Kowakae Higashiosaka, Osaka 577-8502, Japan b Department of Informatics, School of Science and Engineering, Kinki University, 3-4-1 Kowakae Higashiosaka, Osaka 577-8502, Japan |
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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 the subsequent release of nitrogen gas. Through the use of a deuterated triazene, we were able to determine that the reaction proceeds through a 1,2-proton shift. |
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Keywords: | C-C bond forming Dearomatization Nucleophilic addition 1,2-Proton shift Triazene |
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