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N‐Heterocyclic Carbene Complexes of Iron as Photosensitizers for Light‐Induced Water Reduction
Angewandte Chemie International Edition. Categories : Carbenes Organometallic chemistry Functional groups Organic compounds. Namespaces Article Talk. Views Read Edit View history. Languages Add links. Iron, however, has not been developed as a catalyst to the same extent as other transition-metals with regard to use in organic transformations, especially asymmetric processes.
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In a new paper, titled "Iron-catalyzed transformations of diazo compound" and published in the Beijing-headquartered journal National Science Review , scientists Shoufei Zhu and Qilin Zhou, based at Nankai University in the eastern Chinese port city of Tianjin, present an overview on recent advances in the study of iron-catalyzed diazo transformation reactions.
The transition-metal-catalyzed transformations of diazo compounds are widely used in organic synthesis. The catalysts used in the reactions of diazo compounds are generally derived from rhodium, ruthenium, and copper. Iron can undergo facile changes in its oxidation state and exhibit a distinct Lewis acid character.
Iron can catalyze a variety of transformations of diazo compounds please see Scheme 1.
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The iron carbene or carbenoid species may undergo different carbene transfer reactions, including the cyclopropanation of olefins I process c , C-H bond insertion of hydrocarbons II process d , or ylide formation with heteroatom-containing compounds bearing a lone pair III process e. The iron-activated diazo compounds 2 and 2? Furthermore, iron can act as a Lewis acid catalyst and activate electrophiles, such as imines and aldehydes, which react with diazo compound 1 process g. Although an iron-promoted diazo transformation was not discovered until the s, it features some unique advantages.
For example, the iron porphyrins are among the most efficient catalysts for the cyclopropanation reaction of olefins, which exhibit tolerance towards water, as well as several acids and bases; The iron complexes of chiral spiro bisoxazolines afford the highest level of enantioselectivity in the O-H bond insertions of alcohol and water. Other distinct advantages that iron catalysts exhibit over other catalysts are the diazo transformations involving ylide intermediates, such as olefinantion, and the rearrangement of ammonium ylides.
These examples clearly indicate that the potential of iron-catalyzed diazo transformations is huge, although there is still a long way to go. In the future, the development of new and readily tunable iron catalysts will be the key issue in this research field. Materials provided by Science China Press. Note: Content may be edited for style and length.
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Journal Reference : S. Zhu, Q.
Iron-catalyzed transformations of diazo compounds.