Chinese Journal of Organic Chemistry >
Recent Progress in Homogeneous Catalytic Hydrogenation of Nitro Compounds
Received date: 2023-11-05
Revised date: 2023-12-01
Online published: 2023-12-18
Supported by
Natural Science Foundation of Fujian Province(2019J01018)
Amines, particularly primary amines, are a class of important compounds, which are frequently used in the synthesis of pharmaceuticals, agrochemicals, dyes as well as a variety of fine and specialty chemicals. The reduction of nitro compounds is an indispensable route for the production of primary amines, especially aniline and its derivatives. In this context, the catalytic hydrogenation represents the most efficient, atomic economical and environmentally friendly method. In general, the reaction mainly relies on heterogeneous catalysts. And most of the recent reports focus on the development and modification of heterogeneous catalysts. Homogeneous catalysts for the hydrogenation of nitro compounds are scarcely explored. Given the structure of homogeneous metal catalysts can be readily modified and adjusted by the application of different central metal and ligand to regulate the catalytic process, the high efficient and selective reduction can be realized by choosing the appropriate combination of metals and ligands. The development and recent progress of homogeneous catalytic hydrogenation of nitro compounds are systematically summarized, the challenges faced in this field are discussed and a perspective on this topic is made.
Key words: homogeneous catalysis; hydrogenation; nitro compound; amine; chemoselectivity
Mengying Hou , Ai'e Wang , Peiqiang Huang . Recent Progress in Homogeneous Catalytic Hydrogenation of Nitro Compounds[J]. Chinese Journal of Organic Chemistry, 2024 , 44(4) : 1094 -1105 . DOI: 10.6023/cjoc202311006
| [1] | Lawrence S. A. Amines: Synthesis, Properties and Applications, Cambridge University Press, Cambridge, 2004. |
| [2] | (a) Blaser H. U.; Siegrist U.; Steiner H. Fine Chemicals Through Heterogeneous Catalysis, Eds.: Sheldon, R. A.; Van Bekkum, H., Wiley-VCH, Weinheim, 2001, p. 389. |
| [2] | (b) Orlandi M.; Brenna D.; Harms R.; Jost S.; Benaglia M. Org. Process Res. Dev. 2018, 22, 430. |
| [3] | (a) Downing R. S.; Kunkeler P. J.; Van Bekkum H. Catal. Today 1997, 37, 121. |
| [3] | (b) Formenti D.; Ferretti F.; Scharnagl F. K.; Beller M. Chem. Rev. 2019, 119, 2611. |
| [4] | Song J.; Huang Z.-F.; Pan L.; Li K.; Zhang X.; Wang L.; Zou J.-J. Appl. Catal. B: Environ. 2018, 227, 386. |
| [5] | Blaser H.-U.; Steiner H.; Studer M. ChemCatChem 2009, 1, 210. |
| [6] | Li X.; Thakore R. R.; Takale B. S.; Gallou F.; Lipshutz B. H. Org. Lett. 2021, 23, 8114. |
| [7] | Verho O.; Gustafson K. P. J.; Nagendiran A.; Tai C.-W.; B?ckvall J.-E. ChemCatChem 2014, 6, 3153. |
| [8] | Wei H.; Liu X.; Wang A.; Zhang L.; Qiao B.; Yang X.; Huang Y.; Miao S.; Liu J.; Zhang T. Nat. Commun. 2014, 5, 5634. |
| [9] | Fan G.; Huang W.; Wang C. Nanoscale 2013, 5, 6819. |
| [10] | Jagadeesh R. V.; Surkus A.-E.; Junge H.; Pohl M.-M.; Radnik J.; Rabeah J.; Huan H.; Schünemann V.; Brückner A.; Beller M. Science 2013, 342, 1073. |
| [11] | Westerhaus F. A.; Jagadeesh R. V.; Wienh?fer G.; Pohl M.-M.; Radnik J.; Surkus A.-E.; Rabeah J.; Junge K.; Junge H.; Nielsen M.; Brückner A.; Beller M. Nat. Chem. 2013, 5, 537. |
| [12] | Pisiewicz S.; Formenti D.; Surkus A.-E.; Pohl M.-M.; Radnik J.; Junge K.; Topf C.; Bachmann S.; Scalone M.; Beller M. ChemCatChem 2016, 8, 129. |
| [13] | Ye T.-N.; Lu Y.; Li J.; Nakao T.; Yang H.; Tada T.; Kitano M.; Hosono H. J. Am. Chem. Soc. 2017, 139, 17089. |
| [14] | (a) Serna P.; Corma A. ACS Catal. 2015, 5, 7114. |
| [14] | (b) Hu Z.-N.; Liang J.; Ding K.; Ai Y.; Liang Q.; Sun H.-B. Appl. Catal. A: Gen. 2021, 626, 118339. |
| [15] | (a) Haber F.; Elektrochem. Z. Angew. Phys. Chem. 1898, 22, 506. |
| [15] | (b) Dyson R. M.; Hazenkamp M.; Kaufmann K.; Maeder M.; Studer M.; Zilian A. J. Chemom. 2000, 14, 737. |
| [16] | Knifton J. F. J. Org. Chem. 1975, 40, 519. |
| [17] | Knifton J. F. J. Org. Chem. 1976, 41, 1200. |
| [18] | Toti A.; Frediani P.; Salvini A.; Rosi L.; Giolli C. J. Organomet. Chem. 2005, 690, 3641. |
| [19] | Deshmukh A. A.; Prashar A. K.; Kinage A. K.; Kumar R.; Meijboom R. Ind. Eng. Chem. Res. 2010, 49, 12180. |
| [20] | Yao Z. J.; Zhu J. W.; Lin N.; Qiao X. C.; Deng W. Dalton Trans. 2019, 48, 7158. |
| [21] | Chepaikin E. G.; Khidekel M. L. J. Mol. Catal. 1978, 4, 103. |
| [22] | Harsy S. G. Tetrahedron 1990, 40, 7403. |
| [23] | Chugh V.; Chatterjee B.; Chang W.-C.; Cramer H. H.; Hindemith C.; Randel H.; Weyhermüller T.; Farès C.; Werlé C. Angew. Chem., Int. Ed. 2022, 61, e202205515. |
| [24] | Yang S.-T.; Shen P.; Liao B.-S.; Liu Y.-H.; Peng S.-M.; Liu S.-T. Organometallics 2017, 36, 3110. |
| [25] | Corma A.; González-Arellano C.; Iglesias M.; Sánchez F. Appl. Catal.,A 2009, 356, 99. |
| [26] | Deshpande R. M.; Mahajan A. N.; Diwakar M. M.; Ozarde P. S.; Chaudhari R. V. J. Org. Chem. 2004, 69, 4835. |
| [27] | Wienh?fer G.; Baseda-Krüger M.; Ziebart C.; Westerhaus F. A.; Baumann W.; Jackstell R.; Junge K.; Beller M. Chem. Commun. 2013, 49, 9089. |
| [28] | Duan Y.-N.; Zeng Y.; Cui Z.; Wen J.; Zhang X. J. Catal. 2023, 417, 109. |
| [29] | Casewit C. J.; Coons D. E.; Wright L. L.; Miller W. K.; DuBois M. R. Organometallics 1986, 5, 951. |
| [30] | Reis P. M.; Royo B. Tetrahedron Lett. 2009, 50, 949. |
| [31] | Pedrajas E.; Sorribes I.; Gushchin A. L.; Laricheva Y. A.; Junge K.; Beller M.; Llusar R. ChemCatChem 2017, 9, 1128. |
| [32] | Murugesan K.; Wei Z.; Chandrashekhar V. G.; Jiao H.; Beller M.; Jagadeesh R. V. Chem. Sci. 2020, 11, 4332. |
| [33] | Xu M.; Wang Y.; Zhou Y.; Yao Z.-J. J. Organomet. Chem. 2022, 959, 122187. |
| [34] | Zubar V.; Dewanji A.; Rueping M. Org. Lett. 2021, 23, 2742. |
| [35] | Timelthaler D.; Schofberger W.; Topf C. Eur. J. Org. Chem. 2021, 2021, 2114. |
/
| 〈 |
|
〉 |