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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 5: 1786 - 1791

DOI: https://doi.org/10.6023/cjoc202301026

ARTICLES

Rare-Earth Metal Complexes-Catalyzed Dehydropolymerization of Methylamine-Boranes

  • Shengjie Jiang ,
  • Yang Wang ,
  • Xin Xu
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  • Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
* Corresponding author. E-mail:

Received date: 2023-01-30

  Revised date: 2023-03-10

  Online published: 2023-03-31

Supported by

National Natural Science Foundation of China(21871204)

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Abstract

Rare-earth metal complexes-catalyzed dehydropolymerization of amine-borane was achieved. Rare-earth metallo- cene alkyl complexes [(C5Me4R)2LnR', R=Me, H; Ln=Sc, Y; R'=CH2SiMe3, CH(SiMe3)2] were found to be active catalysts for the dehydropolymerization of methylamine-borane (MAB), generating corresponding boron-nitrogen polymer [(MeNHBH2)n, PMAB]. The results showed that the polymerization activity would decrease with the increase of ion radius of the metal center or the decrease of the steric hindrance of the supporting ligands. In the mechanistic study, a β-B-agostic-type scandium amidoborane complex was successfully isolated through the stoichiometric reaction of Sc complex with MAB. Moreover, the control experiment confirmed the existence of scandium hydride species, which may be the catalytic active intermediate.

Key words： rare-earth; amine-borane; dehydrogenation; polymerization; β-hydride elimination

Cite this article

Shengjie Jiang , Yang Wang , Xin Xu . Rare-Earth Metal Complexes-Catalyzed Dehydropolymerization of Methylamine-Boranes[J]. Chinese Journal of Organic Chemistry, 2023 , 43(5) : 1786 -1791 . DOI: 10.6023/cjoc202301026

References

[1]
(a) Staubitz, A.; Robertson, A. P. M.; Sloan, M. E.; Manners, I. Chem. Rev. 2010, 110, 4023.
[1]
(b) Staubitz, A.; Robertson, A. P. M.; Manners, I. Chem. Rev. 2010, 110, 4079.
[1]
(c) Chen, Y.; Liao, Z.; Cao, T.; Zhu, S. Green Synth. Catal. 2021, 2, 145.
[1]
(d) Wang, Q.; Meng, W.; Feng, X.; Du, H. Chin. J. Chem. 2021, 39, 918.
[2]
(a) Staubitz, A.; Presa Soto, A.; Manners, I. Angew. Chem., Int. Ed. 2008, 47, 6212.
[2]
(b) Johnson, H. C.; Robertson, A. P. M.; Chaplin, A. B.; Sewell, L. J.; Thompson, A. L.; Haddow, M. F.; Manners, I.; Weller, A. S. J. Am. Chem. Soc. 2011, 133, 11076.
[3]
(a) Priegert, A. M.; Rawe, B. W.; Serin, S. C.; Gates, D. P. Chem. Soc. Rev. 2016, 45, 922.
[3]
(b) Rossin, A.; Peruzzini, M. Chem. Rev. 2016, 116, 8848.
[3]
(c) Colebatch, A. L.; Weller, A. S. Chem.-Eur. J. 2019, 25, 1379.
[3]
(d) Vidal, F.; J?kle, F. Angew. Chem., Int. Ed. 2019, 58, 5846.
[4]
(a) Manners, I. Dalton Trans. 2016, 45, 1055.
[4]
(b) Wang, X.; Hooper, T. N.; Kumar, A.; Priest, I. K.; Sheng, Y.; Samuels, T. O. M.; Wang, S.; Robertson, A. W.; Pacios, M.; Bhaskaran, H.; Weller, A. S.; Warner, J. H. CrystEngComm 2017, 19, 285.
[5]
(a) Staubitz, A.; Sloan, M. E.; Robertson, A. P. M.; Friedrich, A.; Schneider, S.; Gates, P. J.; Schmedt auf der Günne, J.; Manners, I. J. Am. Chem. Soc. 2010, 132, 13332.
[5]
(b) He, C.; Zhang, Q.; Huo, J.; Fu, L. Chin. Chem. Lett. 2021, 33, 527.
[6]
Metters, O. J.; Chapman, A. M.; Robertson, A. P. M.; Woodall, C. H.; Gates, P. J.; Wass, D. F.; Manners, I. Chem. Commun. 2014, 50, 12146.
[7]
Marziale, A. N.; Friedrich, A.; Klopsch, I.; Drees, M.; Celinski, V. R.; Schmedt auf der Gu?nne, J.; Schneider, S. J. Am. Chem. Soc. 2013, 135, 13342.
[8]
(a) Glu?er, A.; F?rster, M.; Celinski, V. R.; Schmedt Auf Der Gu?nne, J.; Holthausen, M. C.; Schneider, S. ACS Catal. 2015, 5, 7214.
[8]
(b) Anke, F.; Han, D.; Klahn, M.; Spannenberg, A.; Beweries, T. Dalton Trans. 2017, 46, 6843.
[8]
(c) Anke, F.; Boye, S.; Spannenberg, A.; Lederer, A.; Heller, D.; Beweries, T. Chem.-Eur. J. 2020, 26, 7889.
[9]
Boyd, T. M.; Andrea, K. A.; Baston, K.; Johnson, A.; Ryan, D. E.; Weller, A. S. Chem. Commun. 2020, 56, 482.
[10]
Brodie, C. N.; Sotorrios, L.; Boyd, T. M.; Macgregor, S. A.; Weller, A. S. ACS Catal. 2022, 12, 13050.
[11]
(a) Johnson, H. C.; Leitao, E. M.; Whittell, G. R.; Manners, I.; Lloyd-Jones, G. C.; Weller, A. S. J. Am. Chem. Soc. 2014, 136, 9078.
[11]
(b) Colebatch, A. L.; Hawkey Gilder, B. W.; Whittell, G. R.; Oldroyd, N. L.; Manners, I.; Weller, A. S. Chem.-Eur. J. 2018, 24, 5450.
[11]
(c) Adams, G. M.; Colebatch, A. L.; Skornia, J. T.; McKay, A. I.; Johnson, H. C.; Lloyd-Jones, G. C.; Macgregor, S. A.; Beattie, N. A.; Weller, A. S. J. Am. Chem. Soc. 2018, 140, 1481.
[11]
(d) Adams, G. M.; Ryan, D. E.; Beattie, N. A.; McKay, A. I.; Lloyd-Jones, G. C.; Weller, A. S. ACS Catal. 2019, 9, 3657.
[11]
(e) Ryan, D. E.; Andrea, K. A.; Race, J. J.; Boyd, T. M.; Lloyd-Jones, G. C.; Weller, A. S. ACS Catal. 2020, 10, 7443.
[12]
(a) LaPierre, E. A.; Patrick, B. O.; Manners, I. J. Am. Chem. Soc. 2019, 141, 20009.
[12]
(b) Jurca, T.; Dellermann, T.; Stubbs, N. E.; Resendiz-Lara, D. A.; Whittell, G. R.; Manners, I. Chem. Sci. 2018, 9, 3360.
[13]
Trose, M.; Rei?, M.; Rei?, F.; Anke, F.; Spannenberg, A.; Boye, S.; Lederer, A.; Arndt, P.; Beweries, T. Dalton Trans. 2018, 47, 12858.
[14]
Xu, P.; Xu, X. Organometallics 2019, 38, 3212.
[15]
Wang, Y.; Xu, P.; Xu, X. Chin. Chem. Lett. 2021, 32, 4002.
[16]
Stennett, T. E.; Harder, S. Chem. Soc. Rev. 2016, 45, 1112.
[17]
(a) Forster, T. D.; Tuononen, H. M.; Parvez, M.; Roesler, R. J. Am. Chem. Soc. 2009, 131, 6689.
[17]
(b) Wolstenholme, D. J.; Traboulsee, K. T.; Decken, A.; McGrady, G. S. Organometallics 2010, 29, 5769.
[17]
(c) Helten, H.; Dutta, B.; Vance, J. R.; Sloan, M. E.; Haddow, M. F.; Sproules, S.; Collison, D.; Whittell, G. R.; Lloyd-Jones, G. C.; Manners, I. Angew. Chem., Int. Ed. 2013, 52, 437.
[18]
Maity, A.; Teets, T. S. Chem. Rev. 2016, 116, 8873.
[19]
Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Nolan, M. C.; Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203.
[20]
Luo, Y.; Jiang, S.; Xu, X. Angew. Chem., Int. Ed. 2022, 61, e202117750.
[21]
Bhunya, S.; Malakar, T.; Paul, A. Chem. Commun. 2014, 50, 5919.
[22]
Luo, Y.; Teng, H.-L.; Xue, C.; Nishiura, M.; Hou, Z. ACS Catal. 2018, 8, 8027.
[23]
Clair, M. A. St.; Santarsiero, B. D.; Bercaw, J. E. Organometallics 1989, 8, 17.
[24]
Den Haan, K. H.; De Boer, J. L.; Teuben, J. H.; Spek, A. L.; Koji?-Prodi?, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726.
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