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Reactivity‐Controlled Regioselectivity: A Regiospecific Synthesis of 1,2‐Disubstituted Benzimidazoles
Author(s) -
Deng Xiaohu,
Mani Neelakandha S.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901056
Subject(s) - chemoselectivity , regioselectivity , chemistry , reactivity (psychology) , amination , amidine , tandem , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , medicine , materials science , alternative medicine , pathology , composite material
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.