404-65-9Relevant academic research and scientific papers
Photocatalysis Enabling Acceptorless Dehydrogenation of Diaryl Hydrazines at Room Temperature
Sahoo, Manoj K.,Saravanakumar, Krishnasamy,Jaiswal, Garima,Balaraman, Ekambaram
, p. 7727 - 7733 (2018/07/25)
Aromatic azo compounds are privileged structural motifs, and they exhibit a myriad of pharmaceutical as well as industrial applications. Here, we report a catalytic acceptorless dehydrogenation of diarylhydrazine derivatives to access a wide variety of aryl-azo compounds with the removal of molecular hydrogen as the sole byproduct. This distinctive reactivity has been achieved under dual catalytic conditions by merging the visible-light active [Ru(bpy)3]2+ as the photoredox catalyst and Co(dmgH)2(py)Cl as the proton-reduction catalyst. The reaction proceeds smoothly under very mild and benign conditions and operates at ambient temperature. This dual catalytic approach is highly compatible with many different functional groups and has a broad substrate scope. We have also demonstrated the reversible hydrogen storage and release phenomenon on hydrazobenzene/azobenzene couple to show the utility of these compounds as hydrogen storage materials. Further diversification of azobenzene was shown by a transition-metal-catalyzed azo-group-directed ortho-C-H bond functionalization.
Dehydrogenation of the NH?NH Bond Triggered by Potassium tert-Butoxide in Liquid Ammonia
Wang, Lei,Ishida, Akiko,Hashidoko, Yasuyuki,Hashimoto, Makoto
supporting information, p. 870 - 873 (2017/01/14)
A novel strategy for the dehydrogenation of the NH?NH bond is disclosed using potassium tert-butoxide (tBuOK) in liquid ammonia (NH3) under air at room temperature. Its synthetic value is well demonstrated by the highly efficient synthesis of aromatic azo compounds (up to 100 % yield, 3 min), heterocyclic azo compounds, and dehydrazination of phenylhydrazine. The broad application of this strategy and its benefit to chemical biology is proved by a novel, convenient, one-pot synthesis of aliphatic diazirines, which are important photoreactive agents for photoaffinity labeling.
