Citation: Yang Wang, Pengfei Xu, Xin Xu. Dehydrocoupling of boranes with amines using a scandium catalyst[J]. Chinese Chemical Letters, ;2021, 32(12): 4002-4005. doi: 10.1016/j.cclet.2021.05.041 shu

Dehydrocoupling of boranes with amines using a scandium catalyst

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China

xinxu@suda.edu.cn

Received Date: 1 April 2021
Revised Date: 19 May 2021
Accepted Date: 21 May 2021
Available Online: 26 May 2021

Figures(6)

The scandocene alkyl complex (C₅Me₅)₂ScCH₂SiMe₃ was found to be an efficient catalyst for the dehydrocoupling of the non-cyclic boranes, dicyclohexylborane and thexylborane, with amines under mild conditions. The reactions afforded the corresponding aminoboranes in high yields with good functional group tolerance. The stoichiometric reaction of scandium alkyl with amine led to the isolation of a scandium amide complex, which was shown to be an active species during the catalysis. Although a borane-coordinated scandium hydride was also obtained from the stoichiometric experiment, it was not involved in the catalytic cycle. In addition, kinetic studies provided insight into this intermolecular dehydrogenation reaction.
- Borane,
- Aminoborane,
- Dehydrocoupling,
- Scandium,
- β-H elimination
1. [1]
  (a) A. Staubitz, A.P.M. Robertson, Sloan M.E, I. Manners, Chem. Rev. 110 (2010) 4023-4078;
  (b) A.L. Colebatch, A.S. Weller, Chem. Eur. J. 25 (2019) 1379-1390;
  (c) X. Long, C. Dou, J. Liu, L. Wang, Chin. Chem. Lett. 29 (2018) 1343-1346;
  (d) L. Li, Y. Gao, C. Dou, J. Liu, Chin. Chem. Lett. 31 (2020) 1193-1196.
2. [2]
  R.H. Cragg, M.F. Lappert, B.P. Tilley, J. Chem. Soc. (1964) 2108-2115. doi: 10.1039/jr9640002108
3. [3]
  R. Jefferson, M.F. Lappert, B. Prokai, B.P. Tilley, J. Chem. Soc. A (1966) 1584-1590.
4. [4]
  (a) M. Suginome, L. Uehlin, M. Murakami, J. Am. Chem. Soc. 126 (2004) 13196-13197;
  (b) G.P. Junor, E.A. Romero, X. Chen, R. Jazzar, G. Bertrand, Angew. Chem. Int. Ed. 58 (2019) 2875-2878.
5. [5]
  C. Solé, E. Fernández, Angew. Chem. Int. Ed. 125 (2013) 11561-11565. doi: 10.1002/ange.201305098
6. [6]
  (a) E. Chong, S.A. Blum, J. Am. Chem. Soc. 137 (2015) 10144-10147;
  (b) K. Yuan, S. Wang, Org. Lett. 19 (2017) 1462-1465.
7. [7]
  (a) R.A. Bartlett, X. Feng, M.M. Olmstead, P.P. Power, K.J. Weese, J. Am. Chem. Soc. 109 (1987) 4851-4854;
  (b) G. Linti, J. Organomet. Chem. 465 (1994) 79-83;
  (c) H. Chen, R.A. Bartlett, M.M. Olmstead, P.P. Power, S.C. Shoner, J. Am. Chem. Soc. 112 (1990) 1048-1055;
  (d) M. Aman, O. Mrózek, L. Dostál, Z. Růžičková, R. Jambor, J. Organomet. Chem. 872 (2018) 1-7.
8. [8]
  (a) J.F. Janik, C.K. Narula, E.G. Gulliver, E.N. Duesler, R.T. Paine, Inorg. Chem. 27 (1988) 1222-1227;
  (b) B. Wrackmeyer, B. Schwarze, W. Milius, J. Organomet. Chem. 489 (1995) 201-205;
  (c) B. Wrackmeyer, G. Kehr, S.Z. Ali, Z. Naturforsch. 53b (1998) 393-395;
  (d) B. Wrackmeyer, H.E. Maisel, M. Herberhold, J. Organomet. Chem. 637 (2001) 727-732.
9. [9]
  (a) Y. Tang, X. Li, PT CN 101440101, 2009;
  (b) Z. Gao, X. Li, PT CN 102093399, 2011.
10. [10]
  C.C. Chong, R. Kinjo, ACS Catal 5 (2015) 3238-3259. doi: 10.1021/acscatal.5b00428
11. [11]
  (a) E.A. Romero, J.L. Peltier, R. Jazzar, G. Bertrand, Chem. Commun. 52 (2016) 10563-10565;
  (b) C.M. Vogels, P.E. O'Connor, T.E. Phillips, et al., Can. J. Chem. 79 (2001) 1898-1905.
12. [12]
  D.J. Liptrot, M.S. Hill, M.F. Mahon, A.S.S. Wilson, Angew. Chem. Int. Ed. 54 (2015) 13362-13365. doi: 10.1002/anie.201505949
13. [13]
  Z. Yang, M. Zhong, X. Ma, et al., J. Am. Chem. Soc. 138 (2016) 2548-2551. doi: 10.1021/jacs.6b00032
14. [14]
  A. Harinath, S. Anga, T.K. Panda, RSC Adv. 6 (2016) 35648-35653. doi: 10.1039/C6RA04125F
15. [15]
  J.D. Erickson, T.Y. Lai, D.J. Liptrot, M.M. Olmstead, P.P. Power, Chem. Commun. 52 (2016) 13656-13659. doi: 10.1039/C6CC06963K
16. [16]
  M.A. St. Clair, B.D. Santarsiero, J.E. Bercaw, Organometallics 8 (1989) 17-22. doi: 10.1021/om00103a004
17. [17]
  P. Xu, X. Xu, Organometallics 38 (2019) 3212-3217. doi: 10.1021/acs.organomet.9b00461
18. [18]
  (a) X. Han, L. Xiang, Y. Chen, Chem. Eur. J. 23 (2017) 14728-14732;
  (b) J. Chu, X. Han, Y. Chen, et al., J. Am. Chem. Soc. 136 (2014) 10894-10897;
  (c) J. Chu, Q. Zhou, Y. Li, X. Leng, Y. Chen, Sci. China Chem. 57 (2014) 1098-1105.
19. [19]
  (a) F. Bonnet, C.D.C. Violante, M. Visseaux, Chem. Commun. (2009) 3380-3382;
  (b) B.G. Segal, S.J. Lippard, Inorg. Chem. 17 (1978) 844-850.
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