Kharasch addition of tetrachloromethane to alkenes catalyzed by metal acetylacetonates

Catalytic Synthesis and Antifungal Activity of New Polychlorinated Natural Terpenes

“…The synthesis of the target compounds was accomplished using our previously optimized catalytic system for the Kharasch addition of tetrachloromethane to olefins under mild reaction conditions [14]. Using various transition metal acetylacetonates M(acac) (M = Zn, Co, V, Ni, Mo, Mn, Fe, and Cr) and triethylamine as cocatalyst and iron complex highlighting its potential as an effective catalyst, the reactions offer the halogen derivatives in moderate to good yields.…”

“…In a typical experiment, NEt 3 as cocatalyst [14] was added to a solution of Fe(acac) 2 in toluene at 80 ∘ C and after 15 min CCl 4 was added. The reaction mixture was stirred for 30 min and then terpene 1a-f was added.…”

“…On the other hand, it is a synthetically useful process for functionalizing organic compounds by means of halogen derivatives with a high level of atom economy. Kharasch addition is typically catalyzed by transition metal complexes of Cu, Ru, Fe, or Ni [10,[12][13][14]. However, although the Kharasch addition of CCl 4 to simple alkenes has been extensively studied [12][13][14], to our knowledge no works have been devoted to the corresponding reactions using natural terpenic alkenes.…”

“…In the course of our studies on monoterpenes and their derivatives, we have recently reported an extremely efficient method for the preparation of various allylic terpenic chlorides [14,[20][21][22][23]. Following our catalysis objective, we became interested in the preparation of a new class of polychlorinated natural product using Kharasch addition of CCl 4 catalyzed by iron acetylacetonate and to evaluate their inhibition capacity of the growth of the three pathogenic microorganisms.…”

(R)-2-Methyl-5-[(R)-2,4,4,4-tetrachlorobutan-2-yl]cyclohex-2-enone

“…For synthetic details, see: Boualy et al (2011); Dragutan et al (2007). For related structures, see: Boualy et al (2009Boualy et al ( , 2011; Ziyat et al (2004Ziyat et al ( , 2006. For the distribution of caraway (Carum carvi L.), see: Carvalho da & Fonseca da (2006); Hornok (1992).…”