Hydrosilylation Reactions of Alkene with Tertiary Silanes Catalyzed by Iron-Series Metals

  • Wei Sun ,
  • Shoufei Zhu
Expand
  • Frontiers Science Center for New Organic Matter, State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Received date: 2023-05-14

  Revised date: 2023-06-23

  Online published: 2023-07-13

Supported by

National Key R&D Program of China(2021YFA1500200); National Natural Science Foundation of China(92256301); National Natural Science Foundation of China(92156006); National Natural Science Foundation of China(22221002); National Natural Science Foundation of China(21971119); Program of Introducing Talents of Discipline to Universities(111 Project); Program of Introducing Talents of Discipline to Universities(B06005); Haihe Laboratory of Sustainable Chemical Transformations, and the Fundamental Research Funds for the Central Universities, and the XPLORER PRIZE

Abstract

Transition metal-catalyzed hydrosilylation of alkene has become one of the most important and fundamental homogeneous catalytic reactions, however, such reactions still face the problems of massive consumption of precious metal catalysts in industrial applications. Iron-series metals are abundant in the Earth's crust, cheap, easy to obtain, and biocompatible. Compared with precious metals such as platinum, iron-series metals have many advantages as catalysts, but there are still large gaps in catalytic hydrosilylation of alkene and tertiary silanes, especially involving industrial applications of silicones, and cannot replace precious metal catalysts for large-scale industrial production at current stage. The development of new iron-series metal catalysts for the efficient and highly selective hydrosilylation reaction of alkene with tertiary silanes and the in-depth discovery of the regulations on activity and selectivity of the catalysts are of great research value and have become a hot research area with a series of important progresses. The research progress in the hydrosilylation of olefins and tertiary silanes catalyzed by iron-series metals is systematically reviewed, the challenges faced in this field are discussed and the future development direction of this field is also prospected. Only the reactions promoted by homogeneous catalysts are introduced.

Cite this article

Wei Sun , Shoufei Zhu . Hydrosilylation Reactions of Alkene with Tertiary Silanes Catalyzed by Iron-Series Metals[J]. Chinese Journal of Organic Chemistry, 2023 , 43(10) : 3339 -3351 . DOI: 10.6023/cjoc202305016

References

[1]
(a) Marciniec B.; Maciejewski H.; Pietraszok C.; Pawluc P. Advances in Silicone Science, Springer, 2009.
[1]
(b) Obligacion J. V.; Chirik P. J. Nat. Rev. Chem. 2018, 2, 15.
[2]
Speier J. L.; Webster J. A.; Barnes G. H. J. Am. Chem. Soc. 1957, 79, 974.
[3]
Karstedt B. D. US 3775452, 1973.
[4]
Markó I. E.; Stérin S.; Buisine O.; Mignani G.; Branlard P.; Tinant B.; Declercq J.-P. Science 2002, 298, 204.
[5]
Holwell A. J. Platin. Met. Rev. 2008, 52, 243.
[6]
For reviews, see: (a) Sun J.; Deng L. ACS Catal. 2016, 6, 290.
[6]
(b) Du X.-Y.; Huang Z. ACS Catal. 2017, 7, 1227.
[6]
(c) Chen J.-H; Guo J.; Lu Z. Chin. J. Chem. 2018, 36, 1075.
[6]
(d) Almeida L. D. de; Wang H.-L.; Junge K.; Cui X.-J.; Beller M. Angew. Chem., Int. Ed. 2021, 60, 550.
[6]
(e) Zhu S.-F. Chin. J. Chem. 2021, 39, 3211.
[7]
Bauer I.; Kn?lker H.-J. Chem. Rev. 2015, 115, 3170.
[8]
(a) Bart S. C.; Lobkovsky E.; Chirik P. J. J. Am. Chem. Soc. 2004, 126, 13794.
[8]
(b) Chen J.-H.; Cheng B.; Cao M.-Y.; Lu Z. Angew. Chem., Int. Ed. 2015, 54, 4661.
[8]
(c) Du X.-Y.; Zhang Y.-L.; Peng D.-J.; Huang Z. Angew. Chem., Int. Ed. 2016, 55, 6671.
[8]
(d) Docherty J. H.; Peng J.-Y.; Dominey A. P.; Thomas S. P. Nat. Chem. 2017, 9, 595.
[8]
(e) Chen B.; Lu P.; Zhang H.; Cheng X.; Lu Z. J. Am. Chem. Soc. 2017, 139, 9439.
[8]
(f) Hu M.-Y.; He Q.; Fan S.-J.; Wang Z.-C.; Liu L.-Y.; Mu Y.-J.; Peng Q.; Zhu S.-F. Nat. Commun. 2018, 9, 221.
[8]
(g) Cheng B.; Liu W.-B.; Lu Z. J. Am. Chem. Soc. 2018, 140, 5014.
[8]
(h) Hu M.-Y.; Lian J.; Sun W.; Qiao T.-Z.; Zhu S.-F. J. Am. Chem. Soc. 2019, 141, 4579.
[8]
(i) Hu M.-Y.; He P.; Qiao T.-Z.; Sun W.; Li W.-T.; Lian J.; Li J.-H.; Zhu S.-F. J. Am. Chem. Soc. 2020, 142, 16894.
[8]
(j) Sun W.; Li M.-P.; Li L.-J.; Huang Q.; Hu M.-Y.; Zhu S.-F. Chem. Sci. 2022, 13, 2721.
[9]
(a) Freidlina R. K.; Chukovskaya E. T.; Tsao I.; Nesmeyanov A. N. Dokl. Akad. Nauk SSSR 1960, 132, 374.
[9]
(b) Nesmeyanov A. N.; Freidlina R. K.; Chukovskaya E. C.; Petrova R. G.; Belyavsky A. B. Tetrahedron 1962, 17, 61.
[10]
Schroeder M. A.; Wrighton M. S. J. Organomet. Chem. 1977, 128, 345.
[11]
Sunada Y.; Tsutsumi H.; Shigeta K.; Yoshida R.; Hashimoto T.; Nagashima H. Dalton Trans. 2013, 42, 16687.
[12]
Sunada Y.; Noda D.; Soejima H.; Tsutsumi H.; Nagashima H. Organometallics 2015, 34, 2896.
[13]
Noda D.; Tahara A.; Sunada Y.; Nagashima H. J. Am. Chem. Soc. 2016, 138, 2480.
[14]
Sanagawa A.; Nagashima H. Organometallics 2018, 37, 2859.
[15]
Tondreau A. M.; Atienza C. C. H.; Weller K. J.; Nye S. A.; Lewis K. M.; Delis J. G. P.; Chirik P. J. Science 2012, 335, 567.
[16]
Small B. L.; Brookhart M.; Bennett A. M. A. J. Am. Chem. Soc. 1998, 120, 4049.
[17]
Tondreau A. M.; Atienza C. C. H.; Darmon J. M.; Milsmann C.; Hoyt H. M.; Weller K. J.; Nye S. A.; Lewis K. M.; Boyer J.; Delis J. G. P.; Lobkovsky E.; Chirik P. J. Organometallics 2012, 31, 4886.
[18]
Peng D.-J.; Zhang Y.-L.; Du X.-Y.; Zhang L.; Leng X.-B.; Walter M. D.; Huang Z. J. Am. Chem. Soc. 2013, 135, 19154.
[19]
Greenhalgh M. D.; Frank D. J.; Thomas S. P. Adv. Synth. Catal. 2014, 356, 584.
[20]
Jia X.-Q.; Huang Z. Nat. Chem. 2016, 8, 157.
[21]
Kamitani M.; Yujiri K.; Yuge H. Organometallics 2020, 39, 3535.
[22]
Greenwood N. N.; Earnshaw A. Chemistry of the Elements, Butterworth, London, 1997, p. 1114.
[23]
Chalk A. J.; Harrod J. F. J. Am. Chem. Soc. 1965, 87, 1133.
[24]
Magomedov G. K. I.; Andrianov K. A.; Shkolnik O. V.; Izmailov B. A.; Kalinin V. N. J. Organomet. Chem. 1978, 149, 29.
[25]
Stranix B. R.; Liu H.-Q.; Darling G. D. J. Org. Chem. 1997, 62, 6183.
[26]
Chalk A. J.; Harrod J. F. J. Am. Chem. Soc. 1967, 89, 1640.
[27]
(a) Reichel C. L.; Wrighton M. S. Inorg. Chem. 1980, 19, 3858.
[27]
(b) Seitz F.; Wrighton M. S. Angew. Chem., Int. Ed. 1988, 27, 289.
[28]
Brookhart M.; Grant B. E. J. Am. Chem. Soc. 1993, 115, 2151.
[29]
Chen C.; Hecht M. B.; Kavara A.; Brennessel W. W.; Mercado B. Q.; Weix D. J.; Holland P. L. J. Am. Chem. Soc. 2015, 137, 13244.
[30]
Ibrahim A. D.; Entsminger S. W.; Zhu L.-Y.; Fout A. R. ACS Catal. 2016, 6, 3589.
[31]
(a) Schuster C. H.; Diao T.-N.; Pappas I.; Chirik P. J. ACS Catal. 2016, 6, 2632.
[31]
(b) Diao T.-N.; Chirik P. J.; Roy A. K.; Lewis K. M.; Nye S.; Weller K. J.; Delis J. G. P.; Yu R. US 0080536, 2015.
[32]
Lee K. L. Angew. Chem., Int. Ed. 2017, 56, 3665.
[33]
Liu Y.; Deng L. J. Am. Chem. Soc. 2017, 139, 1798.
[34]
Yan Y.; Li J.; Bai Y.; Peng J. Arabian J. Chem. 2023, 16, 104743.
[35]
Cornish A. J.; Lappert M. F.; Nile T. A. J. Organomet. Chem. 1977, 136, 73.
[36]
Pappas I.; Treacy S.; Chirik P. J. ACS Catal. 2016, 6, 4105.
[37]
Srinivas V.; Nakajima Y.; Ando W.; Sato K.; Shimada S. J. Organomet. Chem. 2016, 809, 57.
[38]
Chang A. S-m.; Kawamura K. E.; Henness H. S.; Salpino V. M.; Greene J. C.; Zakharov L. N.; Cook A. K. ACS Catal. 2022, 12, 11002.
Outlines

/