Iodine(III)-mediated halogenations of acyclic monoterpenoids

Laure Peilleron , Tatyana Grayfer (1) , Joëlle Dubois (2) , Robert H Dodd , Kevin Cariou (1) , Open Access

1 ICSN - Institut de Chimie des Substances Naturelles
2 SU FM - Sorbonne Université - Faculté de Médecine

Five different halofunctionalizations of acyclic monoterpenoids were performed using a combination of a hypervalent iodine(III) reagent and a halide salt. In this manner, the dibromination, the bromo(trifluoro)acetoxylation, the bromohydroxylation, the iodo(trifluoro)acetoxylation or the ene-type chlorination of the distal trisubstituted double bond occurred with excellent selectivity and moderate to good yields. 1103

Mots clés: halogenation; hypervalent iodine; monoterpenes

Domaines: Chimie organique

Laure Peilleron, Tatyana Grayfer, Joëlle Dubois, Robert H Dodd, Kevin Cariou, et al.. Iodine(III)-mediated halogenations of acyclic monoterpenoids. Beilstein Journal of Organic Chemistry, 2018, 14, pp.1103-1111. ⟨10.3762/bjoc.14.96⟩. ⟨hal-02307167⟩