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Elsevier, Tetrahedron Letters, 30(54), p. 3982-3984

DOI: 10.1016/j.tetlet.2013.05.070

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Copper(II) chloride promoted transformation of amines into guanidines and asymmetrical N,N′-disubstituted guanidines

Journal article published in 2013 by Brendan Kelly ORCID, Isabel Rozas
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This paper is available in a repository.

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Abstract

We present a concise, less-toxic and broadly applicable method for coupling weakly nucleophilic amines with N,N'-di-(tert-butoxycarbonyl)thiourea, N-(tert-butxoycarbonyl), N'-alkyl/arylsubstituted-thioureas and N,N'-di-(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of copper(II) chloride. Subsequent removal of Boc protecting groups affords guanidines, di-substituted guanidines and 2-aminoimidazolines in modest to excellent overall yields.