Electrochemical Conversion of Phthaldianilides to Phthalazin‐1, 4‐diones by Dehydrogenative N−N Bond Formation. Issue 3 (14th December 2017)

• Record Type: Journal Article
• Authors: Kehl, Anton; Gieshoff, Tile; Schollmeyer, Dieter; Waldvogel, Siegfried R.
• Is Part Of: Chemistry. Volume 24:Issue 3(2018)
• Page Start: 590
• Page End: 593
• Publication Date: 2017-12-14
• Subjects: electrochemistry -- green chemistry -- heterocyclic chemistry -- N, N coupling -- phthalazin-1, 4-diones; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201705578
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The electrochemical synthesis of 6‐membered rings via anodic dianilide N−N coupling is challenging due to concurring benzoxazole co‐formation. The rigidity of the a phthalic acid backbone allows a novel access to phthalazin‐1, 4‐diones by N−N bond formation using anodically generated amidyl radicals. Since conventional synthetic routes to phthalazin‐1, 4‐diones require the use of toxic N, N′ ‐diarylhydrazines and generate reagent waste, a safer and more sustainable approach is required. Easy accessible starting materials, a broad scope of applicable functional groups, promising yields, and a very simple set‐up elevate this sustainable method. Abstract : Direct electrochemical synthesis of phthalazin‐1, 4‐diones was realized by anodic N−N bond generation. Easy accessible phthalic dianilides and a simple electrolysis set‐up ensure a straightforward access to 6‐membered ring systems avoiding the use of highly carcinogenic N, N′ ‐diarylhydrazines as building blocks.