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Room-Temperature Hydrodehalogenation of Halogenated Heteropentalenes with One or Two Heteroatoms

Giorgio Chelucci*, Salvatore Baldino and Andrea Ruiu

*Dipartimento di Agraria, UniversitÓ di Sassari, Viale Italia 39, I-07100 Sassari, Italy, Email:

G. Chelucci, S. Baldino, A. Ruiu, J. Org. Chem., 2012, 77, 9921-9925.

DOI: 10.1021/jo3019335


NaBH4-TMEDA as hydride source and catalytic PdCl2(dppf) in THF is 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 and allow highly chemo- and regioselective reactions.

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Key Words

dehalogenations, sodium borohydride

ID: J42-Y2012-3590