Transition Metal Catalyzed Carbocycle-Selective Asymmetric Hydrogenation of Aromatic Rings

doi:10.6023/cjoc202403017

Abstract

Asymmetric hydrogenation of carbon rings in (hetero)arenes is one of the most direct and efficient methods for preparing saturated and partially saturated chiral six membered carbon ring compounds. While significant challenges in terms of low reactivity and selectivity remain, some breakthroughs have been made in this field of carbocycle-selective asymmetric hydrogenation of (hetero)arenes in recent years. The research progress of transition metal catalyzed carbocycle-selective asymmetric hydrogenation of (hetero)arenes in the past few decades is summarized, and the prospects of further developments are also discussed.

Key words: transition metal, (hetero)arene, asymmetric hydrogenation, dearomatization

Cite this article

Qian Chen, Zhaobin Han, Kuiling Ding. Transition Metal Catalyzed Carbocycle-Selective Asymmetric Hydrogenation of Aromatic Rings[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2063-2076.

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Fig. & Tab. 16

Scheme 1. Chemo-, diastereo- and enantioselectivities in the asymmetric hydrogenation of ortho-substituted benzenes

Scheme 2. Heterogeneous catalytic diastereoselective hydrogenation of (hetero)arenes induced by chiral auxiliaries

Scheme 3. Heterogeneous catalytic diastereoselective hydrogenation of arenes induced by chiral substrate

Scheme 4. Rh complexes 17~19 catalyzed diastereoselective hydrogenation of arenes induced by chiral substrates

Scheme 5. Homogeneous catalytic hydrogenation of (hetero)- arenes with carbocycle selectivity

Scheme 6. Ru/SINpEt catalyzed asymmetric hydrogenation of substituted quinoxalines

Scheme 7. Ru/PhTrap catalyzed asymmetric hydrogenation of substituted naphthalenes

Scheme 8. Ru/PhTrap catalyzed asymmetric hydrogenation of substituted quinolones and isoquinolines

Scheme 9. Ru-catalyzed asymmetric hydrogenation of N-(phenanthren-9-yl)acetamides

Scheme 10. Ru-catalyzed asymmetric hydrogenation of 9-phenanthrols

Scheme 11. Rh-catalyzed asymmetric hydrogenation of substituted anthracenes, naphthalenes and phenanthrenes

Scheme 12. Mo-catalyzed asymmetric hydrogenation of substituted quinolones and naphthalenes

Scheme 13. Complete asymmetric hydrogenation of benzofurans and 2,6-dimethylnaphthalene by relay catalysis

Scheme 14. Complete asymmetric hydrogenation of substituted vinylarenes with homogeneous chiral rhodium complex and heterogeneous rhodium relay catalysis

Scheme 15. Complete asymmetric hydrogenation of substituted indoles and benzofurans using chiral ruthenium complex with dual function

Scheme 16. Asymmetric transfer hydrogenation of substituted naphthols and phenols with cooperative heterogeneous and homogeneous catalysis

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