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Chemoselective amination of 5-bromo-2-chloro-3-fluoropyridine.

Stroup, Bryan, Szklennik, Paul, Forster, Cornelia and Serrano-Wu, Michael (2007) Chemoselective amination of 5-bromo-2-chloro-3-fluoropyridine. Organic Letters, 9 (10). pp. 2039-2042. ISSN 1523-7060


The chemoselective functionalization of 5-bromo-2-chloro-3-fluoropyridine (1c) is described. Catalytic amination conditions (Pd2dba3, Xantphos, base) afford exclusively the bromide substitution product (2) for both secondary amines and primary anilines. A reversal in chemoselectivity is observed under neat conditions in the absence of palladium catalysis, with substitution at the 2-chloro position preferred to generate 3. Last, selective substitution of the 3-fluoro group is achieved under SNAr conditions to afford the dihalo adduct (4).

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Date Deposited: 14 Dec 2009 14:00
Last Modified: 31 Jan 2013 01:17


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