丰产金属催化的碳氮不饱和键不对称氢化反应

doi:10.6023/cjoc202208003

摘要/Abstract

碳氮不饱和键的不对称氢化反应是构建手性胺类化合物一类非常有效的方法. 然而, 已报道的这类反应通常使用储量稀少、毒性较高的贵金属催化剂(钌、铑、铱和钯等). 因此, 利用廉价易得、生物兼容性强的第一过渡周期丰产金属(锰、铁、钴和镍等)替代贵金属发展新型的手性催化剂, 实现含氮不饱和化合物的不对称氢化反应, 对于实现手性含氮精细有机化学品的高效绿色合成具有重要的意义. 近年来, 丰产金属催化碳氮不饱和键的不对称氢化反应取得了长足的发展并展现出广阔的应用前景. 鉴于不同丰产金属催化剂的结构和性质对于催化活性、反应选择性及底物适用范围的显著影响, 文中根据催化剂中心金属元素种类的不同进行分类, 系统综述了丰产金属催化的碳氮不饱和键不对称氢化反应的研究进展.

关键词: 丰产金属催化, 不对称氢化, 碳氮不饱和键

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

引用此文

刘晨光, 刘强. 丰产金属催化的碳氮不饱和键不对称氢化反应[J]. 有机化学, 2022, 42(10): 3213-3220.

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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图/表 12

Figure 1. 过渡金属催化的碳氮不饱和键不对称氢化反应 Transition metal-catalyzed asymmetric hydrogenation of carbon-nitrogen unsaturated bonds系统综述了丰产金属催化的碳氮不饱和键不对称氢化反应的研究进展. 不同于之前报道的相关综述[7], 本综述根据催化剂中心金属元素种类的不同进行分类, 侧重于归纳总结不同丰产金属催化体系在底物适用范围、反应条件以及反应机理等方面的异同.

图2. 碳氮不饱和键不对称氢化反应的两种机理

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

图3. 二茂钛催化亚胺的不对称氢化反应

Figure 3. Titanocene-catalyzed asymmetric hydrogenation of imines

图4. 钴催化二芳基亚胺的不对称氢化反应

Figure 4. Cobalt-catalyzed asymmetric hydrogenation of diaryl imines

图5. 钴催化腙类化合物的不对称氢化反应

Figure 5. Cobalt-catalyzed asymmetric hydrogenation of hydrazones

图6. 镍催化N-磺酰基亚胺的不对称氢化反应

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

图7. 镍催化环状磺酰亚胺与α,β-不饱和亚胺的不对称加氢反应

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

图8. 镍催化环状磺酰亚胺基酯与噁唑-2-酮的不对称氢化反应

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

图9. 镍催化N-芳基亚胺酯的不对称氢化反应

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

图10. 金属/有机小分子协同催化碳氮双键的不对称氢化反应

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

图11. 铁催化亚胺的不对称氢化反应

Figure 11. Iron-catalyzed asymmetric hydrogenation of imines

图12. 锰催化含氮杂环化合物的不对称氢化反应

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

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