Synlett p. 1817 - 1822 (2020)
Update date:2022-08-02
Topics:
Yanagisawa, Akira
Heima, Toshihiko
Watanabe, Kana
Haeno, Shun
The Barbier-type propargylation of azo compounds with α,γ-disubstituted propargylic tosylates was achieved by using metallic barium as the promoter. Various propargylated hydrazines (α-adducts) were exclusively synthesized from the corresponding propargylic tosylates and azobenzenes (diaryldiazenes). The thus-obtained propargylic hydrazines were further efficiently converted into propargylic amines by reductive N-N bond cleavage. Benzidine rearrangement of the propargylic hydrazines was also attempted.
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