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

Giorgio Chelucci*, Salvatore Baldino and Andrea Ruiu

*Dipartimento di Agraria, Università di Sassari, Viale Italia 39, I-07100 Sassari, Italy, Email: chelucciuniss.it

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

DOI: 10.1021/jo3019335

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Abstract

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

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ID: J42-Y2012-3590