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Abstract
A mild and operationally simple deoxygenation of epoxides, sulfoxides, and amine N-oxides is described using a sub-stoichiometric amount of low-valent niobium complexes generated in situ from commercially available NbCl 5 and zinc dust. The deoxygenation proceeds by a reductive cleavage of polarized O–C/O–N/O–S bonds through a single electron transfer from zinc metal to the niobium–substrate complex due to the high oxophilic nature of the niobium species. The presence of adjacent radical-stabilizing groups is beneficial to epoxide substrates; however the similar prerequisite does not apply to sulfoxides and amine N-oxides, where a broad range of substrates are efficiently deoxygenated in excellent yields.
Published Version
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