High Oxidation State Organopalladium(iv) Species: Applications to C–H Activation*,**
Liam K. Burt A B and Curtis C. Ho
A B
+ Author Affiliations
- Author Affiliations
A School of Natural Sciences – Chemistry, University of Tasmania, Hobart, Tas. 7001, Australia.
B Corresponding authors. Email: lburt1@utas.edu.au; curtis.ho@utas.edu.au
Australian Journal of Chemistry 71(10) 753-755 https://doi.org/10.1071/CH18233
Submitted: 21 May 2018 Accepted: 2 July 2018 Published: 14 August 2018
Abstract
This highlight article focuses on some seminal discoveries in organopalladium(iv) chemistry and the implications and notable applications of these findings in contemporary palladium catalysis and in particular C–H activation.
References
[1] R. F. Heck, Ann. N. Y. Acad. Sci. 1977, 295, 201.| Crossref | GoogleScholarGoogle Scholar |
[2] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
| Crossref | GoogleScholarGoogle Scholar |
[3] R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874.
| Crossref | GoogleScholarGoogle Scholar |
[4] N. T. S. Phan, M. V. D. Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609.
| Crossref | GoogleScholarGoogle Scholar |
[5] A. B. Kantchev, C. J. O’Brien, M. G. Organ, Angew. Chem. Int. Ed. 2007, 46, 2768.
| Crossref | GoogleScholarGoogle Scholar |
[6] See p. 189 in: A. J. Canty, Handbook of Organopalladlium Chemistry for Organic Synthesis 2002 (John Wiley & Sons: New York, NY).
[7] W. R. Mason, Inorg. Chem. 1973, 12, 20.
| Crossref | GoogleScholarGoogle Scholar |
[8] R. Usón, P. Royo, F. Martinez, J. Organomet. Chem. 1975, 90, 367.
| Crossref | GoogleScholarGoogle Scholar |
[9] D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1979, 101, 4981.
| Crossref | GoogleScholarGoogle Scholar |
[10] (a) For a selection of reviews on palladium(iv) in catalysis see: K. Muñiz, Angew. Chem. Int. Ed. 2009, 48, 9412.
| Crossref | GoogleScholarGoogle Scholar |
(b) T. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147.
| Crossref | GoogleScholarGoogle Scholar |
(c) A. J. Hickman, M. S. Sanford, Nature 2012, 484, 177.
| Crossref | GoogleScholarGoogle Scholar |
(d) K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788.
| Crossref | GoogleScholarGoogle Scholar |
(e) J. T. Topczewski, M. S. Sanford, Chem. Sci. 2015, 6, 70.
| Crossref | GoogleScholarGoogle Scholar |
[11] P. Sehnal, R. J. K. Taylor, I. J. S. Fairlamb, Chem. Rev. 2010, 110, 824.
| Crossref | GoogleScholarGoogle Scholar |
[12] K. Muñiz, Angew. Chem. Int. Ed. 2009, 48, 9412.
| Crossref | GoogleScholarGoogle Scholar |
[13] P. K. Byers, A. J. Canty, B. W. Skelton, A. H. White, J. Chem. Soc. Chem. Commun. 1986, 1722.
| Crossref | GoogleScholarGoogle Scholar |
[14] A. J. Canty, Acc. Chem. Res. 1992, 25, 83.
| Crossref | GoogleScholarGoogle Scholar |
[15] A. J. Canty, Dalton Trans. 2009, 10409.
| Crossref | GoogleScholarGoogle Scholar |
[16] W. De Graaf, J. Boersma, W. J. J. Smeets, A. L. Spek, G. van Koten, Organometallics 1989, 8, 2907.
| Crossref | GoogleScholarGoogle Scholar |
[17] P. K. Byers, A. J. Canty, M. Crespo, R. J. Puddephatt, J. D. Scott, Organometallics 1988, 7, 1363.
| Crossref | GoogleScholarGoogle Scholar |
[18] P. K. Byers, A. J. Canty, B. W. Skelton, A. H. White, Organometallics 1990, 9, 826.
| Crossref | GoogleScholarGoogle Scholar |
[19] N. R. Deprez, M. S. Sanford, Inorg. Chem. 2007, 46, 1924.
| Crossref | GoogleScholarGoogle Scholar |
[20] N. M. Camasso, A. J. Canty, A. Ariafard, M. S. Sanford, Organometallics 2017, 36, 4382.
| Crossref | GoogleScholarGoogle Scholar |
[21] A. J. Canty, J. Patel, T. Rodemann, J. H. Ryan, B. W. Skelton, A. H. White, Organometallics 2004, 23, 3466.
| Crossref | GoogleScholarGoogle Scholar |
[22] K. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 14047.
| Crossref | GoogleScholarGoogle Scholar |
[23] M. Catellani, M. C. Fagnola, Angew. Chem. Int. Ed. Engl. 1995, 33, 2421.
| Crossref | GoogleScholarGoogle Scholar |
[24] M. Catellani, Synlett 2003, 298.
| Crossref | GoogleScholarGoogle Scholar |
[25] A. R. Dick, K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2004, 126, 2300.
| Crossref | GoogleScholarGoogle Scholar |
[26] J. M. Racowski, N. D. Ball, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18022.
| Crossref | GoogleScholarGoogle Scholar |
[27] A. S. McCall, H. Wang, J. M. Desper, S. Kraft, J. Am. Soc. Chem. 2011, 133, 1832.
[28] J. Vicente, A. Arcas, F. Julia-Hernandez, D. Bautista, Chem. Commun. 2010, 46, 7253.
| Crossref | GoogleScholarGoogle Scholar |
[29] P. L. Alsters, P. F. Engel, M. P. Hogerheide, M. Copijn, A. L. Spek, G. van Koten, Organometallics 1993, 12, 1831.
| Crossref | GoogleScholarGoogle Scholar |
[30] L. R. Gray, D. J. Gulliver, W. Levason, M. Webster, Dalton Trans. 1983, 133.
| Crossref | GoogleScholarGoogle Scholar |
[31] R. Usón, J. Forniés, R. Navarro, J. Organomet. Chem. 1975, 96, 307.
| Crossref | GoogleScholarGoogle Scholar |
[32] N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2010, 132, 2878.
| Crossref | GoogleScholarGoogle Scholar |
[33] Y. Ye, N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2010, 132, 14682.
| Crossref | GoogleScholarGoogle Scholar |
[34] A. J. Canty, A. Ariafard, B. F. Yates, M. S. Sanford, Organometallics 2015, 34, 1085.
| Crossref | GoogleScholarGoogle Scholar |
[35] L. M. Xu, B.-J. Li, Z. Yang, Z.-J. Shi, Chem. Soc. Rev. 2010, 39, 712.
| Crossref | GoogleScholarGoogle Scholar |
[36] J. J. Topczewski, M. S. Sanford, Chem. Sci. 2015, 6, 70.
| Crossref | GoogleScholarGoogle Scholar |
