Chelucci, Giorgio Adolfo and Baldino, Salvatore and Ruiu, Andrea (2012) Room-temperature Hydrodehalogenation of halogenated heteropentalenes with one or two heteroatoms. The Journal of Organic Chemistry, Vol. 77 (21), p. 9921-9925. eISSN 1520-6904. Article.
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The pair NaBH4–TMEDA as a hydride source and catalytic PdCl2(dppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes with one or two heteroatoms, while Pd(OAc)2/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.
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