Hurtley reactions

The reaction on unactivated halides can also be done with copper halide catalysts (the Hurtley reaction), and with palladium complex catalysts. 

A modified Hurtley reaction (Scheme 29) on n-bromo-aldo- or -keto-oximes (131 R = H or Me) provides ready access to 3-hydroxy-isoquinoline N-oxides (132 R = H or Me R" = Ac, Bz, COaEt, or CN). °"... 

No reactions of 269 with correspondingly strong and sterically hindered bases and no H-D exchange experiments have so far been reported.165a In the paper published in 1926 by Hurtley and Smiles,m however, the authors described results that could be explained by deprotonation of the benzo-l,3-dithiolium ion (284) (which should be a weaker acid than 269, owing to the fused aromatic ring) to the benzodithiocarbene (285). 

Abstract Although requiring the use of stoichiometric amounts of metal and harsh conditions, the copper-mediated coupling reactions of aryl halides with amines and phenols (Ullmann craidensatiOTis), amides and carbamates (Ullmann-Goldberg condensations), or activated methylene compounds (Ullmann-Hurtley condensations) have been for a long time useful methods for the formation of C(aryl)-N, C(aryl)-0, and C(aryl)-C bonds. In 2001, a renaissance of the Ullmann reaction has been initiated with the discovery of versatile new copper catalytic systems for C-C, C-N, or C-O coupling under mild temperature ccmditions. 

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