Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 4, Pages 680-686Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901056
Keywords
Regioselectivity; Copper catalysis; Amination; Heterocycles
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We demonstrate exceptional levels of regioselectivity in the tandem amination reactions between 1,2-differentiated dihaloarenes and N-substituted amidines. The regiochemical outcome of this CuI-catalyzed reaction is achieved through a combination of N-1/N-2 chemoselectivity on the amidine and reactivity-controlled X-1/X-2 chemoselectivity on the 1,2-dihaloarene. This reaction proves to be fairly general for the regiospecific synthesis of 1,2-substituted benzimidazoles.
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