Iron-Catalyzed Arylmagnesiation of Aryl(alkyl)acetylenes in the Presence of an N-Heterocyclic Carbene Ligand

Abstract

Addition of arylmagnesium bromides to aryl(alkyl)acetylenes proceeded in the presence of an iron catalyst and a N-heterocyclic carbene ligand to give high yields of the corresponding alkenylmagnesium reagents, which were transformed into tetrasubstituted alkenes by subsequent treatment with electrophiles. [reaction: see text]

Iron Catalysis in Organic Synthesis

“…679 In general, the yields were superior as compared to the FeÀCu cocatalyzed variant; however, the diastereoselectivity was less pronounced. Tetrasubstituted olefins could be constructed by quenching the intermediate carbometalated products with electrophiles such as allyl bromide and iodine.…”

Polymer precursors from catalytic reactions of natural oils

“…301 Finally, the arylmagnesiation of aryl(alkyl)acetylenes was reported to be catalysed by NHC-Fe catalysts. 302 It was attempted to synthesise the complex [Fe(IPr)(CO) Finally, the last metal from this group, iridium, deserved some studies dealing with the NHC transfer, considering its general Chemistry is very similar to the one of rhodium.…”

Iron Catalysis in Synthetic Chemistry

“…While studying the dihydroxylation of trans-2-heptene with H 2 O 2 as oxidant, 12% ee for the epoxide byproduct was observed. In 2007, Beller and co-workers (135) developed an efficient method for iron-catalyzed asymmetric epoxidation using H 2 O 2 as oxidant in the presence of a chiral sulfoxamide ligand (58). Various internal alkenes were tolerated under this protocol with good-to-excellent enantioselectivity (Table XVI).…”