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ortho-Perfluoroalkylation and Ethoxycarbonyldifluoromethylation of Aromatic Triazenes

ortho-Perfluoroalkylation and Ethoxycarbonyldifluoromethylation of Aromatic Triazenes

Andreas Hafner, Angela Bihlmeier, Martin Nieger, Wim Klopper, Stefan Bräse

J Org Chem. 2013 Aug 16;78(16):7938-48.

PMID: 23848397

Abstract:

A robust protocol for perfluoroalkylation and ethoxycarbonyldifluoromethylation of functionalized aromatic triazenes is described. Using silver(I)-fluoride and different fluorinated (trimethyl)silyl substituted species, it was possible to synthesize various ortho-fluorinated triazenes in good yields via simple CH-substitution. Initial reactions under solvent-free (neat) conditions indicate a stabilizing interaction between "AgRf" and the triazene moiety, which may be responsible for the good yields and regioselectivity. The transformation possibilities of the triazene moiety make these reactions interesting for the synthesis of fluorinated building blocks. In addition, quantum chemical calculations suggest that the stabilization of the radical intermediate in the ortho-position is distinctly more favored for aromatic triazenes than for other aromatic substrates.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7775419	Silver(I) fluoride		7775-41-9	Price

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