Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Regioselective Sulfenylation of α′-CH3 or α′-CH2 Groups of α,β-Unsaturated Ketones with Heterocyclic Thiols

Regioselective Sulfenylation of α′-CH3 or α′-CH2 Groups of α,β-Unsaturated Ketones with Heterocyclic Thiols
Yogesh Siddaraju, Kandikere Ramaiah Prabhu
A rare regioselective sulfenylation of α′-CH3 or α′-CH2 bonds adjacent to α,β-unsaturated ketones using dimethyl sulfoxide as an oxidant and a substoichiometric amount of aq HI as an additive is described. This methodology employs a strong acid such as aq HI or iodine and exhibits a high regioselectivity without undergoing conjugate addition, which is difficult to achieve under the cross dehydrogenative coupling method.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b03290

DOI: 10.1021/acs.joc.7b03290

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