Abstract
The bis(imino)pyridine iron complex, for the first time, is developed as an effective metal carbene catalyst for carbene transfer reactions of donor-acceptor diazo compounds. Its broad catalytic capability is demonstrated by a range of metal carbene reactions, from cyclopropanation, cyclopropenation, epoxidation, and Doyle-Kirmse reaction to O-H insertion, N-H insertion, and C-H insertion reactions. The asymmetric cyclopropanation of styrene and methyl phenyldiazoacetate was successfully achieved by the new chiral bis(imino)pyridine iron catalyst, which delivers a new gateway for the development of chiral iron catalysis for metal carbene reactions.
Highlights
Transition-metal-catalyzed carbene transfer reactions occurring through metal carbene intermediates encompass a vast array of reactants and catalysts to achieve novel and selective strategies for organic synthesis.[1]
For the rst time, bis(imino)pyridine iron complexes serving as effective catalysts for a range of metal carbene reactions under mild reaction conditions, including cyclopropanation/cyclopropenation, epoxidation, Doyle– Kirmse reaction, O–H insertion, N–H insertion, and C–H insertion (Scheme 1)
A new chiral bis(imino)pyridine ligand derivatized from L-valine methyl ester has been synthesized, and the corresponding enantiopure, C1-symmetric iron catalyst enabled the asymmetric cyclopropanation of styrene and phenyl diazoacetate
Summary
Transition-metal-catalyzed carbene transfer reactions occurring through metal carbene intermediates encompass a vast array of reactants and catalysts to achieve novel and selective strategies for organic synthesis.[1]. For the rst time, bis(imino)pyridine iron complexes serving as effective catalysts for a range of metal carbene reactions under mild reaction conditions (at room temperature or 40 C), including cyclopropanation/cyclopropenation, epoxidation, Doyle– Kirmse reaction, O–H insertion, N–H insertion, and C–H insertion (Scheme 1). To the best of our knowledge, this bis(imino)pyridine iron catalyst represents the most broad-ranging catalytic activity towards metal carbene reactions of diazo compounds over the previously reported iron catalysis system.[6]
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