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IBX‐Mediated Dehydrogenation of Substituted β‐Oxonitriles
Author(s) -
Klahn Philipp,
Kirsch Stefan F.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402007
Subject(s) - dehydrogenation , chemistry , enol , phenols , organic chemistry , catalysis
A convenient method for the mild dehydrogenation of β‐oxonitriles is presented. When treated with o ‐iodoxybenzoic acid (IBX), a range of these compounds were transformed into their unsaturated counterparts. Furthermore, we show that the products of the dehydrogenation can react in situ, undergoing rapid hetero‐Diels–Alder reactions with enol ethers to give multiply substituted dihydropyrans. We also describe the dehydrogenation of cyclic β‐oxonitriles, which leads to the formation of substituted phenols.