Earth-Abundant Metal-Catalyzed Asymmetric Hydrogenation of Carbon-Nitrogen Unsaturated Bonds

doi:10.6023/cjoc202208003

Abstract

Asymmetric hydrogenation of carbon-nitrogen unsaturated bonds is an effective method for the construction of chiral amines. However, most of the known examples rely on the use of noble metal (ruthenium, rhodium, iridium, palladium, etc.) catalysts. Therefore, the replacement of noble-metals by earth-abundant and biocompatible first-row transition metals (manganese, iron, cobalt, nickel, etc.) for the development of new catalysts in asymmetric hydrogenation reactions is of great significance towards sustainable synthesis of chiral nitrongen-containing fine chemicals. In recent years, earth-abundant metal catalyzed asymmetric hydrogenation of unsaturated bonds has witnessed significant progress and shown broad prospects for its applications. Considering that the structures and properties of different earth-abundant metal catalysts have remarkable influence on the reactivity, selectivity, and substrate generality of the target transformations, this review provides an overview of earth-abundant metal catalyzed asymmetric hydrogenation of carbon-nitrogen unsaturated bonds categorized according to the types of central metals in catalysts.

Key words: earth-abundant transition metal catalysis, asymmetric hydrogenation, carbon-nitrogen unsaturated bonds

Cite this article

Chenguang Liu, Qiang Liu. Earth-Abundant Metal-Catalyzed Asymmetric Hydrogenation of Carbon-Nitrogen Unsaturated Bonds[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3213-3220.

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Fig. & Tab. 12

Figure 2. Two types of reaction mechanisms of transition metal- catalyzed asymmetric hydrogenation of carbon-nitrogen unsaturated bonds

Figure 3. Titanocene-catalyzed asymmetric hydrogenation of imines

Figure 4. Cobalt-catalyzed asymmetric hydrogenation of diaryl imines

Figure 5. Cobalt-catalyzed asymmetric hydrogenation of hydrazones

Figure 6. Nickel-catalyzed asymmetric hydrogenation of N- sulfonyl imines

Figure 7. Nickel-catalyzed asymmetric hydrogenation of cyclic sulfamidate imines and α,β-unsaturated ketoimines

Figure 8. Nickel-catalyzed asymmetric hydrogenation of cyclic N-sulfonyl ketimino esters and 2-oxazolones

Figure 9. Nickel-catalyzed asymmetric hydrogenation of N-aryl imino esters

Figure 10. Cooperative transition-metal and organo catalysis for asymmetric hydrogenation of C=N bond

Figure 11. Iron-catalyzed asymmetric hydrogenation of imines

Figure 12. Manganese-catalyzed asymmetric hydrogenation of N-heterocycles

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