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Copper‐Catalyzed Multicomponent Coupling of Organoindium Reagents with Nitrogen‐Containing Aromatic Heterocycles
Author(s) -
Beveridge Ramsay E.,
Black Daniel A.,
Arndtsen Bruce A.
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.201000231
Subject(s) - benzothiazole , benzoxazole , chemistry , reagent , pyridine , combinatorial chemistry , catalysis , organic chemistry , nitrogen , copper , coupling reaction , phthalazine
A mild, copper‐catalyzed coupling of organoindium reagents with nitrogen‐containing aromatic heterocycles and chloroformates is described. This reaction proceeds with a range of organoindium reagents, yielding predominately or exclusively the 1,4‐addition products with pyridine. In addition, a range of other nitrogen‐containing heterocycles can be employed in this reaction (e.g. benzoxazole, benzothiazole, phthalazine). As an illustration of the utility of this reaction, this heterocycle functionalization is coupled with a subsequent oxidation to achieve the one‐pot synthesis of functionalized pyridine and benzothiazole derivatives.