Skip to main content
SpringerLink
Log in

Reaction of o-aminophenol and o-aminobenzyl alcohol with palladium(II) bis(isocyanide) complexes

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Reactions of palladium(II) bis-isocyanide complexes cis-[PdCl2(CNR)2] (R = 2,6-Me2C6H3, 2-Me-6-ClC6H3) with an equimolar amount of chelating N,O-binucleophiles, 2-aminophenol and (2-aminophenyl)-methanol, in acetonitrile at room temperature in 24 h selectively afforded the corresponding open-chain monocarbene complexes. The complexation involved one isocyanide ligand and amino group of the aromatic amine. Neither bis(carbene) complexes (in the reactions with 4 equiv of the nucleophile under harsh conditions) nor C,O-chelate structures were detected. The isolated complexes were characterized by elemental analyses, IR, NMR, and mass spectra, and X-ray diffraction data.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Crociani, B., Boschi, T., and Belluco, U., Inorg. Chem., 1970, vol. 9, no. 9, p. 2021. doi 10.1021/ic50091a013

    Article  CAS  Google Scholar 

  2. Crociani, B., Boschi, T., Nicolini, M., and Belluco, U., Inorg. Chem., 1972, vol. 11, no. 6, p. 1292. doi 10.1021/ic50112a028

    Article  CAS  Google Scholar 

  3. Crociani, B., Uguagliati, P., and Belluco, U., J. Organomet. Chem., 1976, vol. 117, no. 2, p. 189. doi 10.1016/S0022-328X(00)87271-X

    Article  CAS  Google Scholar 

  4. Rotondo, E., Cusumano, M., Crociani, B., Uguagliati, P., and Belluco, U., J. Organomet. Chem., 1977, vol. 134, no. 2, p. 249. doi 10.1016/S0022-328X(00)81424-2

    Article  CAS  Google Scholar 

  5. Michelin, R.A., Pombeiro, A.J.L., and Guedes da Silva, M.F.C., Coord. Chem. Rev., 2001, vol. 218, p. 75. doi 10.1016/S0010-8545(01)00358-7

    Article  CAS  Google Scholar 

  6. Boyarskiy, V.P., Bokach, N.A., Luzyanin, K.V., and Kukushkin, V.Y., Chem. Rev., 2015, vol. 115, p. 2698. doi 10.1021/cr500380d

    Article  CAS  Google Scholar 

  7. Kinzhalov, M.A. and Boyarskiy, V.P., Russ. J. Gen. Chem., 2015, vol. 85, no. 10, p. 2313. doi 10.1134/S1070363215100175

    Article  CAS  Google Scholar 

  8. Boyarskiy, V.P., Luzyanin, K.V., and Kukushkin, V.Yu., Coord. Chem. Rev., 2012, vol. 256, p. 2029. doi 10.1016/j.ccr.2012. 04.022

    Article  CAS  Google Scholar 

  9. Slaughter, L.M., ACS Catal., 2012, vol. 2, p. 1802. doi 10.1021/cs300300y

    Article  CAS  Google Scholar 

  10. Luzyanin, K.V., Tskhovrebov, A.G., Carias, M.C., Guedes da Silva, M.F.C., Pombeiro, A.J.L., and Kukushkin, V.Y., Organometallics, 2009, vol. 28, p. 6559. doi 10.1021/om900682v

    Article  CAS  Google Scholar 

  11. Kinzhalov, M.A., Luzyanin, K.V., Boyarskiy, V.P., Haukka, M., and Kukushkin, V.Y., Organometallics, 2013, vol. 32, p. 5212. doi 10.1021/om4007592

    Article  CAS  Google Scholar 

  12. Miltsov, S.A., Karavan, V.S., Boyarsky, V.P., Gomez-de Pedro, S., Alonso-Chamarro, J., and Puyol, M., Tetrahedron Lett., 2013, vol. 54, p. 1202. doi 10.1016/j.tetlet.2012.12.060

    Article  CAS  Google Scholar 

  13. Anisimova, T.B., Guedes da Silva, M.F.C., Kukushkin, V.Yu., Pombeiro, A.J.L., and Luzyanin, K.V., Dalton Trans., 2014, vol. 43, p. 15861. doi 10.1039/C4DT01917B

    Article  CAS  Google Scholar 

  14. Savicheva, E.A., Kurandina, D.V., Nikiforov, V.A., and Boyarskiy, V.P., Tetrahedron Lett., 2014, vol. 55, p. 2101. doi 10.1016/j.tetlet.2014.02.044

    Article  CAS  Google Scholar 

  15. Valishina, E.A., Guedes da Silva, M.F.C., Kinzhalov, M.A., Timofeeva, S.A., Buslaeva, T.M., Haukka, M., Pombeiro, A.J.L., Boyarskiy, V.P., Kukushkin, V.Y., and Luzyanin, K.V., J. Mol. Catal. A: Chem., 2014, vol. 395, p. 162. doi 10.1016/j.molcata. 2014.08.018

    Article  CAS  Google Scholar 

  16. Timofeeva, S.A., Kinzhalov, M.A., Valishina, E.A., Luzyanin, K.V., Boyarskiy, V.P., Buslaeva, T.M., Haukka, M., and Kukushkin, V.Y., J. Catal., 2015, vol. 329, p. 449. doi 10.1016/j.jcat.2015. 06.001

    Article  CAS  Google Scholar 

  17. Mikhaylov, V.N., Sorokoumov, V.N., Korvinson, K.A., Novikov, A.S., and Balova, I.A., Organometallics, 2016, vol. 35, no. 11, p. 1684. doi 10.1021/acs.organomet.6b00144

    Article  CAS  Google Scholar 

  18. Kinzhalov, M.A., Timofeeva, S.A., Luzyanin, K.V., Boyarskiy, V.P., Yakimanskiy, A.A., Haukka, M., and Kukushkin, V.Yu., Organometallics, 2016, vol. 35, no. 2, p. 218. doi 10.1021/acs. organomet.5b00936

    Article  CAS  Google Scholar 

  19. Luzyanin, K.V., Pombeiro, A.J.L., Haukka, M., and Kukushkin, V.Yu., Organometallics, 2008, vol. 27, no. 20, p. 5379. doi 10.1021/om800517c

    Article  CAS  Google Scholar 

  20. Tskhovrebov, A.G., Luzyanin, K.V., Kuznetsov, M.L., Sorokoumov, V.N., Balova, I.A., Haukka, M., and Kukushkin, V.Y., Organometallics, 2011, vol. 30, no. 4, p. 863. doi 10.1021/om101041g

    Article  CAS  Google Scholar 

  21. Tskhovrebov, A.G., Luzyanin, K.V., Dolgushin, F.M., Guedes da Silva, M.F.C., Pombeiro, A.J.L., and Kukushkin, V.Y., Organometallics, 2011, vol. 30, no. 12, p. 3362. doi 10.1021/om2002574

    Article  CAS  Google Scholar 

  22. Kinzhalov, M.A., Boyarskiy, V.P., Luzyanin, K.V., Haukka, M., and Kukushkin, V.Yu., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, no. 3, p. 758. doi 10.1007/s11172-013-0103-4

    Article  CAS  Google Scholar 

  23. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, no. 12, p. S1. doi 10.1039/P298700000S1

  24. Kinzhalov, M.A., Boyarskiy, V.P., Luzyanin, K.V., Dolgushin, F.M., and Kukushkin, V.Y., Dalton Trans., 2013, vol. 42, no. 29, p. 10394. doi 10.1039/c3dt51335a

    Article  CAS  Google Scholar 

  25. Kinzhalov, M.A., Luzyanin, K.V., Boyarskaya, I.A., Starova, G.L., and Boyarskiy, V.P., J. Mol. Struct., 2014, vol. 1068, p. 222. doi 10.1016/j.molstruc.2014.04.025

    Article  CAS  Google Scholar 

  26. Moncada, A.I., Manne, S., Tanski, J.M., and Slaughter, L.M., Organometallics, 2006, vol. 25, no. 2, p. 491. doi 10.1021/om050786f

    Article  CAS  Google Scholar 

  27. Kinzhalov, M.A., Zolotarev, A.A., and Boyarskiy, V.P., J. Struct. Chem., 2016, vol. 57, no. 4, p. 822. doi 10.1134/S0022476616040302

    Article  Google Scholar 

  28. Chay, R.S., Luzyanin, K.V., Kukushkin, V.Y., Guedes da Silva, M.F.C., and Pombeiro, A.J.L., Organometallics, 2012, vol. 31, no. 6, p. 2379. doi 10.1021/om300020j

    Article  CAS  Google Scholar 

  29. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008. vol. 64, p. 112. doi 10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  30. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, no. 2, p. 339. doi 10.1107/S0021889808042726

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State University, Universitetskaya nab. 7–9, St. Petersburg, 199034, Russia

    M. A. Kinzhalov, G. L. Starova & V. P. Boyarskii

  2. Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014, Jyväskylä, Finland

    M. Haukka

Authors
  1. M. A. Kinzhalov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. L. Starova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Haukka
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. P. Boyarskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. P. Boyarskii.

Additional information

Original Russian Text © M.A. Kinzhalov, G.L. Starova, M. Haukka, V.P. Boyarskii, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 10, pp. 1703–1708.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kinzhalov, M.A., Starova, G.L., Haukka, M. et al. Reaction of o-aminophenol and o-aminobenzyl alcohol with palladium(II) bis(isocyanide) complexes. Russ J Gen Chem 86, 2350–2355 (2016). https://doi.org/10.1134/S1070363216100170

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363216100170

Keywords

Search

Navigation