A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones

Lucile Anthore (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

A convergent synthesis of trifluoromethyl ketones and alpha beta-unsaturated trifluoromethyl ketones is described, starting with aliphatic iodides and dithiocarbonates (xanthates) and exploiting both the alpha- and beta-fragmentations of a sulfonyl radical. The transformation initially furnishes the ketones in a masked enol carbonate form, from which they can be easily regenerated.

Domains: Chemical Sciences; Organic chemistry

Lucile Anthore, Samir Z. Zard. A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones. Organic Letters, 2015, 17 (12), pp.3058-3061. ⟨10.1021/acs.orglett.5b01344⟩. ⟨hal-01186604⟩