Abstract
Three new Pd-pyridine enhanced precatalyst preparation stabilization and initiation(PEPPSI) complexes with halogen groups on the N-heterocyclic carbene and pyridine were prepared. Their structures have been clearly characterized by nuclear magnetic resonance spectroscopy and X-ray single-crystal diffraction. The effects of the electronic properties of halogen groups on the catalytic activity in the Suzuki-Miyaura cross-coupling of aryl chlorides were investigated. These Pd-PEPPSI complexes could catalyze the cross-coupling reaction efficiently with a low catalyst loading(0.05%, molar ratio) at room temperature and the products were obtained in high yields.
This is a preview of subscription content, log in to check access.
References
- [1]
Negishi E. I., de Meijere A., Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, Inc., New York., 2002
- [2]
de Meijere A., Diederich F., Metal-catalyzed Cross-coupling Reactions, 2nd Edition, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2014
- [3]
Arduengo A. J., Harlow R. L., Kline M., J. Am. Chem. Soc., 1991, 113(1), 361
- [4]
Fantasia S., Petersen J. L., Jacobsen H., Cavallo L., Nolan S. P., Organometallics, 2007, 26(24), 5880
- [5]
Jones W. D., J. Am. Chem. Soc., 2009, 131(42), 15075
- [6]
Hopkinson M. N., Richter C., Schedler M., Glorius F., Nature, 2014, 510, 485
- [7]
Vummaleti S. V. C., Nelson D. J., Poater A., Adrián G. S., Cordes D. B., Slawin A. M. Z., Nolan S. P., Cavallo L., Chemical Science, 2015, 6, 1895
- [8]
Kantchev E. A., O’Brien C. J., Organ M. G., Angew. Chem., Int. Ed., 2007, 46(16), 2768
- [9]
Würtz S., Glorius F., Acc. Chem. Res., 2008, 41(11), 1523
- [10]
Fortman G. C., Nolan S. P., Chem. Soc. Rev., 2011, 40(10), 5151
- [11]
Froese R. D. J., Lombardi C., Pompeo M., Rucker R. P., Organ M. G., Acc. Chem. Res., 2017, 50(9), 2244
- [12]
Li G., Shi S., Lei P., Szostak M., Advanced Synthesis & Catalysis, 2018, 360(7), 1538
- [13]
Marion N., Nolan S. P., Acc. Chem. Res., 2008, 41(11), 1440
- [14]
Calimsiz S., Sayah M., Mallik D., Organ M. G., Angew. Chem., Int. Ed., 2010, 49(11), 2014
- [15]
Valente C., Calimsiz S., Hoi K. H., Mallik D., Sayah M., Organ M. G., Angew. Chem. Int. Ed., 2012, 51(14), 3314
- [16]
Liu G., Liu C., Zhao X., Wang J., RSC Adv., 2016, 6(50), 44475
- [17]
Liu G., Liu C., Han F., Wang Z., Wang J., Tetrahedron Lett., 2017, 58(8), 726
- [18]
Liu C., Liu G., Zhao H., Chin. J. Chem., 2016, 34(10), 1048
- [19]
Lan X. B., Chen F. M., Ma B. B., Shen D. S., Liu F. S., Organometallics, 2016, 35(22), 3852
- [20]
Ormerod D., Dorbec M., Merkul E., Kaval N., Lefèvre N., Hostyn S., Eykens L., Lievens J., Sergeyev S., Maes B. U. W., Org. Process Res. Dev., 2018, 22, 1509
- [21]
O’Brien C. J., Kantchev E. A. B., Valente C., Hadei N., Chass G. A., Lough A., Hopkinson A. C., Organ M. G., Chem. Eur. J., 2006, 12(18), 4743
- [22]
Rajabia F., Thiel W. R., Adv. Synth. Catal., 2014, 356, 1873
- [23]
Nasielski J., Hadei N., Achonduh G., Kantchev E. A. B., O’Brien C. J., Lough A., Organ M. G., Chem. Eur. J., 2010, 16(35), 10844
- [24]
Organ M. G., Calimsiz S., Sayah M., Hoi K. H., Lough A. J., Angew. Chem. Int. Ed., 2009, 48(13), 2383
- [25]
Valente C., Belowich M. E., Hadei N., Organ M. G., Eur. J. Org. Chem., 2010, 2010(23), 4343
- [26]
Tu T., Sun Z., Fang W., Xu M., Zhou Y., Org. Lett., 2012, 14(16), 4250
- [27]
Lu D. D., He X. X., Liu F. S., J. Org. Chem., 2017, 82(20), 10898
- [28]
Ouyang J. S., Li Y. F., Huang F. D., Lu D. D., Liu F. S., ChemCat-Chem., 2018, 10(2), 371
- [29]
He X. X., Li Y., Ma B. B., Ke Z., Liu F. S., Organometallics., 2016, 35(16), 2655
- [30]
Dunsford J. J., Cavell K. J., Organometallics., 2014, 33(11), 2902
- [31]
Han F., Xu Y., Zhu R., Liu G., Chen C., Wang J., New J. Chem., 2018, 42(9), 7422
- [32]
Türkmen H., Çetinkaya B., J. Organomet Chem., 2006, 691(18), 3749
- [33]
Sheldrick G. M., SHELXL-97, Program for X-Ray Crystal Structure Solution, University of Göttingen, Göttingen, 1997
- [34]
Dolomanov O. V., Bourhis L. J., Gildea R. J., Howard J. A. K., Puschmann H., J. Appl. Cryst., 2009, 42, 339
- [35]
Dash C., Shaikh M. M., Ghosh P., Eur. J. Inorg. Chem., 2009, 2009(12), 1608
- [36]
Organ M. G., Chass G. A., Fang D. C., Hopkinson A. C., Valente C., Synthesis, 2008, 17, 2776
Author information
Affiliations
Corresponding authors
Additional information
Supported by the Natural Science Foundation of Tianjin City, China(No.16JCYBJC19700), the National Natural Science Foundation of China(No.21771138), and the Foundation of Development Program of Future Expert in Tianjin Normal University, China(No.WLQR201704).
Rights and permissions
About this article
Cite this article
Zhang, Y., Han, F., Zhang, M. et al. Highly Active Pd-PEPPSI Complexes for Suzuki-Miyaura Cross-coupling of Aryl Chlorides: an Investigation on the Effect of Electronic Properties. Chem. Res. Chin. Univ. 36, 859–864 (2020). https://doi.org/10.1007/s40242-019-9222-2
Received:
Accepted:
Published:
Issue Date:
Keywords
- Pd-pyridine enhanced precatalyst preparation stabilization and initiation(PEPPSI) complex; Suzu-ki-Miyaura cross-coupling reaction
- Aryl chloride