Journal
HELVETICA CHIMICA ACTA
Volume 100, Issue 10, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.201700199
Keywords
N-heterocycles; Saturated N-heterocycles; Aldehydes; SnAP reagents; Cross-coupling; Radicals
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Funding
- European Research Council (ERC Starting Grant) [306793-CASAA]
- Development and Promotion of Science and Technology Talents Project (DPST), Thailand
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SnAP (Sn (tin) amine protocol) hydrazine reagents and aldehydes undergo oxidative, copper mediated coupling to form substituted 1,4,5-oxadiazepanes and 1,2,5-triazepanes. Unlike all prior reactions involving SnAP reagents, the SnAP hydrazine reagents undergo a molecular oxygen-assisted oxidative cyclization. The air- and moisture tolerant transformation accommodates a broad range of groups including electron-rich, electron-poor aromatic, heteroaromatic, and aliphatic aldehydes and is amenable to gram scale synthesis. These unusual, chiral heterocycles have unexpectedly large optical rotations, which may find use in optical materials.
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