Photocatalysis enabling acceptorless dehydrogenation of diaryl hydrazines at room temperature

TitlePhotocatalysis enabling acceptorless dehydrogenation of diaryl hydrazines at room temperature
Publication TypeJournal Article
Year of Publication2018
AuthorsSahoo, MK, Saravanakumar, K, Jaiswal, G, Balaraman, E
JournalACS Catalysis
Volume8
Issue8
Pagination7727-7733
Date PublishedAUG
Type of ArticleArticle
ISSN2155-5435
Keywordsacceptorless dehydrogenation, Azo benzene, dual catalysis, Hydrogen, photoredox catalysis
Abstract

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.

DOI10.1021/acscatal.8b01579
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)11.384
Divison category: 
Organic Chemistry

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