Synthesis and chemical reactivity of new zinc porphyrin diazoacetates catalyzed by ruthenium and iron porphyrins

Daniel Carrié (1) , Hassan Srour (1) , Paul Le Maux (1) , Gérard Simonneaux (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

Zinc porphyrin diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N’-ditosylhydrazine in ∼70% yield. The transfer of carbenoids derived from the porphyrin diazo compounds catalyzed by metalloporphyrins (Ru,Fe) undergoes dimerization, cyclopropanation, N-H and S-H insertion reactions, respectively

Keywords: Ruthenium porphyrin; Meso-phenyl-diazo-porphyrin ester; Catalytic carbene transfer; iron porphyrin

Domains: Life Sciences [q-bio]; Pharmaceutical sciences; Chemical Sciences

Daniel Carrié, Hassan Srour, Paul Le Maux, Gérard Simonneaux. Synthesis and chemical reactivity of new zinc porphyrin diazoacetates catalyzed by ruthenium and iron porphyrins. Tetrahedron Letters, 2016, 57 (10), pp. 1179-1182. ⟨10.1016/j.tetlet.2016.02.010⟩. ⟨hal-01269738⟩