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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 11: 3335 - 3344

DOI: https://doi.org/10.6023/cjoc202403024

REVIEW

Advances in Homogeneous Hydrogenation of Esters to Alcohols by Non-noble Metal Complexes

  • Xiaolong Fang ,
  • Yu Zhang ,
  • Tao Wang ,
  • Bin Li ,
  • Ning Duan ,
  • Fengjun Zhang
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  • a Key Laboratory of Functional Molecule Design and Interface Process, Anhui Province Engineering Laboratory of Advanced Building Materials, Anhui Jianzhu University, Hefei 230601
    b Key Laboratory of Light Energy Conversion Materials of Hunan Province College, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081
*Corresponding author. E-mail:

Received date: 2024-03-19

  Revised date: 2024-05-07

  Online published: 2024-05-30

Supported by

National Natural Science Foundation of China(21802010); Anhui Provincial Natural Science Foundation(2308085MB49); Anhui Provincial Fund for Outstanding Young Scholars(2023AH030038); Anhui Provincial Fund for Outstanding Young Scholars(gxyq2022027); Key Program of Hunan Education Committee(23A0089); Measurement Funding of Hunan Normal University(23CSY016)

Fold

Abstract

Catalytic hydrogenation of esters to alcohols is a green, sustainable, and atom-economic methodology for alcohol perparation. In the last two decades, the application of noble metal complexes (Ru(II), Ir(III), Os(II), etc.) in homogeneous catalytic hydrogenation of esters to alcohols has achieved significant progress. Replacing noble metals with abundant and environmentally friendly, non-noble metals has been becoming a hot spot. The progress in recent years on the homogeneous catalytic hydrogenation of esters to alcohols is summarized based on non-noble metal complexes including Fe(II), Co(II), and Mn(I). The relationship between complex structure and performance, as well as the catalytic hydrogenation reaction mechanism is detailed discussed to find out the key factors affecting the performance of the complexes, which provides new ideas for further design and development of excellent non-noble metal catalysts.

Key words： non-noble metal; ester; homogeneous catalytic hydrogenation; synergistic effect

Cite this article

Xiaolong Fang , Yu Zhang , Tao Wang , Bin Li , Ning Duan , Fengjun Zhang . Advances in Homogeneous Hydrogenation of Esters to Alcohols by Non-noble Metal Complexes[J]. Chinese Journal of Organic Chemistry, 2024 , 44(11) : 3335 -3344 . DOI: 10.6023/cjoc202403024

References

[1]
(a) Dub P. A.; Ikariya T. ACS Catal. 2012, 2, 1718.
[1]
(b) Clarke M. L. Catal. Sci. Technol. 2012, 2, 2418.
[1]
(c) Li W.; Xie J.-H.; Yuan M. L.; Zhou Q. L. Green. Chem. 2014, 16, 4081.
[1]
(d) Gu X.; Li X.; Xie J.; Zhou Q. Acta Chim. Sinica 2019, 77, 598 (in Chinese).
[1]
(顾雪松, 李校根, 谢建华, 周其林, 化学学报, 2019, 77, 598.)
[2]
Ohkuma T.; Ooka H.; Ikariya T.; Noyori R. J. Am. Chem. Soc. 1995, 117, 10417.
[3]
(a) Noyori R.; Ohkuma T. Angew. Chem., Int. Ed. 2001, 40, 40.
[3]
(b) Noyori R. Angew. Chem., Int. Ed. 2002, 41, 2008.
[3]
(c) Sandoval C. A.; Ohkuma T.; Mu?iz K.; Noyori R. J. Am. Chem. Soc. 2003, 125, 13490.
[3]
(d) Zhao B.; Han Z.; Ding K. Angew. Chem., Int. Ed. 2013, 52, 4744.
[3]
(e) Werkmeister S.; Junge K.; Beller M. Org. Process Res. Dev. 2014, 18, 289.
[4]
Zhang J.; Leitus G.; Ben-David Y.; Milstein D. Angew. Chem., Int. Ed. 2006, 45, 1113.
[5]
Saudan L. A.; Saudan C. M.; Debieux C.; Wyss P. Angew. Chem., Int. Ed. 2007, 46, 7473.
[6]
Kuriyama W.; Matsumoto T.; Ogata O.; Ino Y.; Aoki K.; Tanaka S.; Ishida K.; Kobayashi T.; Sayo N.; Saito T. Org. Process Res. Dev. 2012, 16, 166.
[7]
(a) Sun Y.; Koehler C.; Tan R.; Annibale V. T.; Song D. Chem. Commun. 2011, 47, 8349.
[7]
(b) Spasyuk D.; Gusev D. G. Organometallics 2012, 31, 5239.
[7]
(c) Spasyuk D.; Smith S.; Gusev D. G. Angew. Chem., Int. Ed. 2012, 51, 2772.
[7]
(d) Yue H.; Zhao Y.; Ma X.; Gong J. Chem. Soc. Rev. 2012, 41, 4218.
[7]
(e) Chen T.; Li H.; Qu S.; Zheng B.; He L.; Lai Z.; Wang Z. X.; Huang K. W. Organometallics 2014, 33, 4152.
[7]
(f) Spasyuk D.; Vicent C.; Gusev D. G. J. Am. Chem. Soc. 2015, 137, 3743.
[7]
(g) Tan X.; Wang Y.; Liu Y.; Wang F.; Shi L.; Lee K.-H.; Lin Z.; Lv H.; Zhang X. Org. Lett. 2015, 17, 454.
[7]
(h) Wang F.; Tan X.; Lv H.; Zhang X. Chem.-Asian J. 2016, 11, 2103.
[8]
(a) Clarke Z. E.; Maragh P. T.; Dasgupta T. P.; Gusev D. G.; Lough A. J.; Abdur-Rashid K. Organometallics 2006, 25, 4113.
[8]
(b) Bertoli M.; Choualeb A.; Lough A. J.; Moore B.; Spasyuk D.; Gusev D. G. Organometallics 2011, 30, 3479.
[8]
(c) Acosta-Ramirez A.; Bertoli M.; Gusev D. G.; Schlaf M. Green Chem. 2012, 14, 1178.
[8]
(d) Otsuka T.; Ishii A.; Dub P. A.; Ikariya T. J. Am. Chem. Soc. 2013, 135, 9600.
[8]
(e) Junge K.; Wendt B.; Jiao H.; Beller M. ChemCatChem 2014, 6, 2810.
[8]
(f) Ogata O.; Nakayama Y.; Nara H.; Fujiwhara M.; Kayaki Y. Org. Lett. 2016, 18, 3894.
[9]
Werkmeister S.; Junge K.; Wendt B.; Alberico E.; Jiao H.; Baumann W.; Junge H.; Gallou F.; Beller M. Angew. Chem., Int. Ed. 2014, 53, 8722.
[10]
(a) Chakraborty S.; Dai H.; Bhattacharya P.; Fairweather N. T.; Gibson M. S.; Krause J. A.; Guan H. J. Am. Chem. Soc. 2014, 136, 7869.
[10]
(b) Qu S.; Dai H.; Dang Y.; Song C.; Wang Z. X.; Guan H. ACS Catal. 2014, 4, 4377.
[11]
Elangovan S.; Wendt B.; Topf C.; Bachmann S.; Scalone M.; Spannenberg A.; Jiao H.; Baumann W.; Junge K.; Beller M. Adv. Synth. Catal. 2016, 358, 820.
[12]
Elangovan S.; Garbe M.; Jiao H.; Spannenberg A.; Junge K.; Beller M. Angew. Chem., Int. Ed. 2016, 55, 15364.
[13]
Yuwen J.; Chakraborty S.; Brennessel W. W.; Jones W. D. ACS Catal. 2017, 7, 3735.
[14]
John J. M.; Takebayashi S.; Dabral N.; Miskolzie M.; Bergens S. H. J. Am. Chem. Soc. 2013, 135, 8578.
[15]
Junge K.; Wendt B.; Cingolani A.; Spannenberg A.; Wei Z.; Jiao H.; Beller M. Chem.-Eur. J. 2018, 24, 1046.
[16]
(a) Zhang G.; Hanson S. K. Org. Lett. 2013, 15, 650.
[16]
(b) R?sler S.; Ertl M.; Irrgang T.; Kempe R. Angew. Chem., Int. Ed. 2015, 54, 15046.
[16]
(c) Zhang G.; Yin Z.; Zheng S. Org. Lett. 2016, 18, 300.
[16]
(d) Mastalir M.; Tomsu G.; Pittenauer E.; Allmaier G.; Kirchner K. Org. Lett. 2016, 18, 3462.
[17]
Zhong R.; Wei Z.; Zhang W.; Liu S.; Liu Q. Chem 2019, 5, 1552.
[18]
Yang W.; Chernyshov I. Y.; van Schendel R. K.; Weber M.; Müller C.; Filonenko G. A.; Pidko E. A. Nat. Commun. 2021, 12, 12.
[19]
Yang W.; Kalavalapalli T. Y.; Krieger A. M.; Khvorost T. A.; Chernyshov I. Y.; Weber M.; Uslamin E. A.; Pidko E. A.; Filonenko G. A. J. Am. Chem. Soc. 2022, 144, 8129.
[20]
Wei Z.; Li H.; Wang Y.; Liu Q. Angew. Chem., Int. Ed. 2023, 62, e202301042.
[21]
(a) Gunanathan C.; Ben-David Y.; Milstein D. Science 2007, 317, 790.
[21]
(b) Gnanaprakasam B.; Zhang J.; Milstein D. Angew. Chem., Int. Ed. 2010, 49, 1468.
[21]
(c) Gunanathan C.; Gnanaprakasam B.; Iron M. A.; Shimon L. J.; Milstein D. J. Am. Chem. Soc. 2010, 132, 14763.
[21]
(d) Balaraman E.; Gunanathan C.; Zhang J.; Shimon L. J.; Milstein D. Nat. Chem. 2011, 3, 609.
[22]
Zell T.; Ben‐David Y.; Milstein D. Angew. Chem., Int. Ed. 2014, 53, 4685.
[23]
Srimani D.; Mukherjee A.; Goldberg A. F.; Leitus G.; Diskin‐ Posner Y.; Shimon L. J.; Ben David Y.; Milstein D. Angew. Chem., Int. Ed. 2015, 54, 12357.
[24]
Espinosa‐Jalapa N. A.; Nerush A.; Shimon L. J.; Leitus G.; Avram L.; Ben‐David Y.; Milstein D. Chem.-Eur. J. 2017, 23, 5934.
[25]
(a) Widegren M. B.; Harkness G. J.; Slawin A. M.; Cordes D. B.; Clarke M. L. Angew. Chem., Int. Ed. 2017, 56, 5825.
[25]
(b) Widegren M. B.; Clarke M. L. Org. Lett. 2018, 20, 2654.
[26]
Li X. G.; Li F.; Xu Y.; Xiao L. J.; Xie J. H.; Zhou Q. L. Adv. Synth. Catal. 2022, 364, 744.
[27]
Zubar V.; Lichtenberger N.; Schelwies M.; Oeser T.; Hashmi A. S. K.; Schaub T. ChemCatChem 2022, 14, e202101443.
[28]
Teunissen H. T.; Elsevier C. J. Chem. Commun. 1997, 667.
[29]
(a) Hanton M. J.; Tin S.; Boardman B. J.; Miller P. J. Mol. Catal. A: Chem. 2011, 346, 70.
[29]
(b) Geilen F. M.; Engendahl B.; Ho?lscher M.; Klankermayer J.; Leitner W. J. Am. Chem. Soc. 2011, 133, 14349.
[29]
(c) Wesselbaum S.; Vom Stein T.; Klankermayer J.; Leitner W. Angew. Chem., Int. Ed. 2012, 51, 7499.
[29]
(d) Vom Stein T.; Meuresch M.; Limper D.; Schmitz M.; Ho?lscher M.; Coetzee J.; Cole-Hamilton D. J.; Klankermayer J. R.; Leitner W. J. Am. Chem. Soc. 2014, 136, 13217.
[30]
Korstanje T. J.; van der Vlugt J. I.; Elsevier C. J.; de Bruin B. Science 2015, 350, 298.
[31]
(a) Takebayashi S.; Bergens S. H. Organometallics 2009, 28, 2349.
[31]
(b) Kuriyama W.; Ino Y.; Ogata O.; Sayo N.; Saito T. Adv. Synth. Catal. 2010, 352, 92.
[31]
(c) Stempfle F.; Quinzler D.; Heckler I.; Mecking S. Macromolecules 2011, 44, 4159.
[31]
(d) Furst M. R.; Le Goff R.; Quinzler D.; Mecking S.; Botting C. H.; Cole-Hamilton D. J. Green Chem. 2012, 14, 472.
[31]
(e) Fang X.; Zhang C.; Chen J.; Zhu H.; Yuan Y. RSC Adv. 2016, 6, 45512.
[31]
(f) Fang X.; Li B.; Zheng J.; Wang X.; Zhu H.; Yuan Y. Dalton Trans. 2019, 48, 2290.
[31]
(g) Fang X. L.; Li B.; Jin J.; Duan N. Chin. J. Org. Chem. 2022, 42, 1407 (in Chinese).
[31]
(方霄龙, 李斌, 金杰, 段宁, 有机化学, 2022, 42, 1407.)
[32]
Van Putten R.; Uslamin E. A.; Garbe M.; Liu C.; Gonzalez‐de‐Castro A.; Lutz M.; Junge K.; Hensen E. J.; Beller M.; Lefort L.; Pidko E. A. Angew. Chem., Int. Ed. 2017, 56, 7531.
[33]
(a) Hamilton R. J.; Bergens S. H. J. Am. Chem. Soc. 2006, 128, 13700.
[33]
(b) Fang X.; Duan N.; Zhang M.; Zhang C.; Liu R.; Zhu H. Chin. J. Org. Chem. 2019, 39, 1450 (in Chinese).
[33]
(方霄龙, 段宁, 章敏, 张春燕, 刘睿, 朱红平, 有机化学, 2019, 39, 1450.)
[34]
(a) Langer R.; Iron M. A.; Konstantinovski L.; Diskin‐Posner Y.; Leitus G.; Ben‐David Y.; Milstein D. Chem.-Eur. J. 2012, 18, 7196.
[34]
(b) Hoyt J. M.; Shevlin M.; Margulieux G. W.; Krska S. W.; Tudge M. T.; Chirik P. J. Organometallics 2014, 33, 5781.
[34]
(c) Lagaditis P. O.; Sues P. E.; Sonnenberg J. F.; Wan K. Y.; Lough A. J.; Morris R. H. J. Am. Chem. Soc. 2014, 136, 1367.
[34]
(d) Thai T. T.; Mérel D. S.; Poater A.; Gaillard S.; Renaud J. L. Chem.-Eur. J. 2015, 21, 7066.
[34]
(e) Gajewski P.; Renom‐Carrasco M.; Facchini S. V.; Pignataro L.; Lefort L.; de Vries J. G.; Ferraccioli R.; Piarulli U.; Gennari C. Eur. J. Org. Chem. 2015, 2015, 5526.
[34]
(f) Rosas-Hernández A.; Alsabeh P. G.; Barsch E.; Junge H.; Ludwig R.; Beller M. Chem. Commun. 2016, 52, 8393.
[34]
(g) Hodgkinson R.; Del Grosso A.; Clarkson G.; Wills M. Dalton Trans. 2016, 45, 3992.
[35]
Gajewski P.; Gonzalez‐de‐Castro A.; Renom‐Carrasco M.; Piarulli U.; Gennari C.; de Vries J. G.; Lefort L.; Pignataro L. ChemCatChem 2016, 8, 3431.
[36]
Azouzi K.; Pedussaut L.; Pointis R.; Bonfiglio A.; Kumari Riddhi R.; Duhayon C.; Bastin S.; Sortais J. B. Organometallics 2023, 42, 1832.
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