Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1094-1105.DOI: 10.6023/cjoc202311006 Previous Articles Next Articles
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收稿日期:
2023-11-05
修回日期:
2023-12-01
发布日期:
2023-12-15
基金资助:
Mengying Hou, Ai'e Wang(), Peiqiang Huang()
Received:
2023-11-05
Revised:
2023-12-01
Published:
2023-12-15
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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.
[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.
|
(b) Orlandi M.; Brenna D.; Harms R.; Jost S.; Benaglia M. Org. Process Res. Dev. 2018, 22, 430.
doi: 10.1021/acs.oprd.6b00205 |
|
[3] |
(a) Downing R. S.; Kunkeler P. J.; Van Bekkum H. Catal. Today 1997, 37, 121.
doi: 10.1016/S0920-5861(97)00005-9 pmid: 30516963 |
(b) Formenti D.; Ferretti F.; Scharnagl F. K.; Beller M. Chem. Rev. 2019, 119, 2611.
doi: 10.1021/acs.chemrev.8b00547 pmid: 30516963 |
|
[4] |
Song J.; Huang Z.-F.; Pan L.; Li K.; Zhang X.; Wang L.; Zou J.-J. Appl. Catal. B: Environ. 2018, 227, 386.
doi: 10.1016/j.apcatb.2018.01.052 |
[5] |
Blaser H.-U.; Steiner H.; Studer M. ChemCatChem 2009, 1, 210.
doi: 10.1002/cctc.v1:2 |
[6] |
Li X.; Thakore R. R.; Takale B. S.; Gallou F.; Lipshutz B. H. Org. Lett. 2021, 23, 8114.
doi: 10.1021/acs.orglett.1c03258 |
[7] |
Verho O.; Gustafson K. P. J.; Nagendiran A.; Tai C.-W.; Bäckvall J.-E. ChemCatChem 2014, 6, 3153.
doi: 10.1002/cctc.v6.11 |
[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.
doi: 10.1038/ncomms6634 |
[9] |
Fan G.; Huang W.; Wang C. Nanoscale 2013, 5, 6819.
doi: 10.1039/c3nr01532g |
[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.
doi: 10.1126/science.1242005 |
[11] |
Westerhaus F. A.; Jagadeesh R. V.; Wienhöfer 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.
doi: 10.1038/nchem.1645 pmid: 23695637 |
[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.
doi: 10.1002/cctc.v8.1 |
[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.
doi: 10.1021/jacs.7b08252 |
[14] |
(a) Serna P.; Corma A. ACS Catal. 2015, 5, 7114.
doi: 10.1021/acscatal.5b01846 |
(b) Hu Z.-N.; Liang J.; Ding K.; Ai Y.; Liang Q.; Sun H.-B. Appl. Catal. A: Gen. 2021, 626, 118339.
doi: 10.1016/j.apcata.2021.118339 |
|
[15] |
(a) Haber F.; Elektrochem. Z. Angew. Phys. Chem. 1898, 22, 506.
|
(b) Dyson R. M.; Hazenkamp M.; Kaufmann K.; Maeder M.; Studer M.; Zilian A. J. Chemom. 2000, 14, 737.
doi: 10.1002/(ISSN)1099-128X |
|
[16] |
Knifton J. F. J. Org. Chem. 1975, 40, 519.
doi: 10.1021/jo00892a034 |
[17] |
Knifton J. F. J. Org. Chem. 1976, 41, 1200.
doi: 10.1021/jo00869a025 |
[18] |
Toti A.; Frediani P.; Salvini A.; Rosi L.; Giolli C. J. Organomet. Chem. 2005, 690, 3641.
doi: 10.1016/j.jorganchem.2005.04.045 |
[19] |
Deshmukh A. A.; Prashar A. K.; Kinage A. K.; Kumar R.; Meijboom R. Ind. Eng. Chem. Res. 2010, 49, 12180.
doi: 10.1021/ie1015969 |
[20] |
Yao Z. J.; Zhu J. W.; Lin N.; Qiao X. C.; Deng W. Dalton Trans. 2019, 48, 7158.
doi: 10.1039/C8DT02677G |
[21] |
Chepaikin E. G.; Khidekel M. L. J. Mol. Catal. 1978, 4, 103.
doi: 10.1016/0304-5102(78)80003-0 |
[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.
doi: 10.1002/anie.v61.36 |
[24] |
Yang S.-T.; Shen P.; Liao B.-S.; Liu Y.-H.; Peng S.-M.; Liu S.-T. Organometallics 2017, 36, 3110.
doi: 10.1021/acs.organomet.7b00460 |
[25] |
Corma A.; González-Arellano C.; Iglesias M.; Sánchez F. Appl. Catal.,A 2009, 356, 99.
doi: 10.1016/j.apcata.2008.12.026 |
[26] |
Deshpande R. M.; Mahajan A. N.; Diwakar M. M.; Ozarde P. S.; Chaudhari R. V. J. Org. Chem. 2004, 69, 4835.
pmid: 15230611 |
[27] |
Wienhöfer G.; Baseda-Krüger M.; Ziebart C.; Westerhaus F. A.; Baumann W.; Jackstell R.; Junge K.; Beller M. Chem. Commun. 2013, 49, 9089.
doi: 10.1039/c3cc42983k |
[28] |
Duan Y.-N.; Zeng Y.; Cui Z.; Wen J.; Zhang X. J. Catal. 2023, 417, 109.
doi: 10.1016/j.jcat.2022.11.036 |
[29] |
Casewit C. J.; Coons D. E.; Wright L. L.; Miller W. K.; DuBois M. R. Organometallics 1986, 5, 951.
doi: 10.1021/om00136a019 |
[30] |
Reis P. M.; Royo B. Tetrahedron Lett. 2009, 50, 949.
doi: 10.1016/j.tetlet.2008.12.038 |
[31] |
Pedrajas E.; Sorribes I.; Gushchin A. L.; Laricheva Y. A.; Junge K.; Beller M.; Llusar R. ChemCatChem 2017, 9, 1128.
doi: 10.1002/cctc.v9.6 |
[32] |
Murugesan K.; Wei Z.; Chandrashekhar V. G.; Jiao H.; Beller M.; Jagadeesh R. V. Chem. Sci. 2020, 11, 4332.
doi: 10.1039/D0SC01084G |
[33] |
Xu M.; Wang Y.; Zhou Y.; Yao Z.-J. J. Organomet. Chem. 2022, 959, 122187.
doi: 10.1016/j.jorganchem.2021.122187 |
[34] |
Zubar V.; Dewanji A.; Rueping M. Org. Lett. 2021, 23, 2742.
doi: 10.1021/acs.orglett.1c00659 |
[35] |
Timelthaler D.; Schofberger W.; Topf C. Eur. J. Org. Chem. 2021, 2021, 2114.
doi: 10.1002/ejoc.202100073 pmid: 34248412 |
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