Skip to main content
SpringerLink
Log in

Trends in the chemistry of mono- to multimetal π-arene complexes of chromium and manganese

  • Review
  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

The preparation and the features of the ring activation in π-arene metal (chromium, manganese) complexes are discussed. The bottom-up approach to the synthesis of σ, π-bi- and multimetal complexes, and the synthesis of cyclometallated and multicyclic complexes from a variety of selected routes are also reviewed. The stereochemical features of such complexes, and their applications in carbon–carbon coupling reactions and metal insertion reactions are highlighted. The redox reactivities and selected applications of (multi)metal π-arene complexes in catalysis and organic synthesis are included. Finally, the extension of the multimetal π-arene complexes to larger assemblies is shown. The importance of arene ring substituents in the basic mononuclear units and their use as bidentate metalloligands, with bidentate amines as linkers, in the construction of polymers, metal organic frameworks, networks (also on nanoparticles or silica supports), is highlighted.

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

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Fig. 3
Scheme 18
Scheme 19
Fig. 4
Scheme 20
Scheme 21
Scheme 22
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Scheme 23

Similar content being viewed by others

References

  1. E.L. Muetterties, J.R. Bleeke, E.J. Wucherer, T.A. Albright, Chem. Rev. 82(490), 490 (1982)

    Google Scholar 

  2. R.P. Pike, D.A. Sweigart, Coord. Chem. Rev. 187, 183 (1999)

    Article  CAS  Google Scholar 

  3. R. Pape, K.P. Kaliappan, E.P. Kündig, Chem. Rev. 100, 2917 (2000)

    Article  CAS  Google Scholar 

  4. F. Rose-Munch, E. Rose, Eur. J. Inorg. Chem. (6), 1269 (2002)

  5. H.G. Jahr, M. Nieger, K.H. Dötz, Chem. Eur. J. 11, 5333 (2005)

    Article  CAS  Google Scholar 

  6. M. Oh, K. Yu, H. Li, E.J. Watson, G.B. Carpenter, D.A. Sweigart, Adv. Synth. Catal. 345, 1053 (2003)

    Article  CAS  Google Scholar 

  7. M. Oh, G.B. Carpenter, D.A. Sweigart, Organometallics 21, 1290 (2002)

    Article  CAS  Google Scholar 

  8. M. Oh, G.B. Carpenter, D.A. Sweigart, Acc. Chem. Res. 37, 1 (2004)

    Article  CAS  Google Scholar 

  9. S.B. Kim, D.A. Sweigart, S. Lotz, Encyclopedia of Inorganic Chemistry (Wiley, New York, 2008), p. 775

    Google Scholar 

  10. J.A. Reingold, S.U. Son, C.A. Dullaghan, M. Oh, S.B. Kim, G.B. Carpenter, D.A. Sweigart, Dalton Trans. (20), 2385 (2006)

  11. S.B. Kim, R.D. Pike, J. D’Acchioli, B.J. Walder, G.B. Carpenter, D.A. Sweigart, Angew. Chem. Int. Ed. Engl. 48, 1762 (2009)

    Article  CAS  Google Scholar 

  12. S.B. Kim, R.D. Pike, D.A. Sweigart, Acc. Chem. Res. (2013). doi:101021/ar300353n

    Google Scholar 

  13. C.A.L. Mahaffy, P. Pauson, Inorg. Synth. 28, 137 (1990)

    Google Scholar 

  14. G.A. Moser, M.D. Rausch, Synth. React. Inorg. Met. Org. Chem. 4, 1974 (37)

    Google Scholar 

  15. G.R. Knox, D.G. Leppard, P.L. Pauson, W.E. Watts, J. Organomet. Chem. 34, 347 (1972)

    Article  CAS  Google Scholar 

  16. S.B. Kim, S. Lotz, S. Sun, Y.K. Chung, R.D. Pike, D. Sweigart, Inorg. Synth. 35, 114 (2010)

    CAS  Google Scholar 

  17. Auffrant, D. Prim, F. Rose-Munch, E. Rose, S. Schouteeten, J. Vaissermann, Organometallics 22, 1898 (2003)

    Article  CAS  Google Scholar 

  18. M. Oh, J.A. Reingold, D.A. Sweigart, Coord. Chem. Rev. 248, 561 (2004)

    Article  CAS  Google Scholar 

  19. Sun, L.K. Yeung, D.A. Sweigart, T.-Y. Lee, S.S. Lee, Y.K. Chung, S.R. Switzer, R.D. Pike, Organometallics 14, 2613 (1995)

    Article  CAS  Google Scholar 

  20. M. Rosillo, G. Domingues, J. Pérez-Castells, Chem. Soc. Rev. 36, 1589 (2007)

    Article  CAS  Google Scholar 

  21. H. Woolford, M.R.J. Elsegood, G.W. Weaver, RSC Adv. 2, 6049 (2012)

    Article  CAS  Google Scholar 

  22. F. Rose-Munch, E. Rose, Modern Arene Chemistry, ed. by D. Astruc (Wiley-VCH, Weinheim, 2003) p 368

  23. S.E. Gibson, H. Ibrahim, Chem. Commun. 21, 2465 (2002)

    Google Scholar 

  24. K.H. Dötz, J. Stendel, M. Nieger, Z. Anorg, Allg. Chem. 615, 221 (2009)

    Google Scholar 

  25. K.H. Dötz, J. Stendel, S. Müller, M. Nieger, S. Ketrat, M. Dolg, Organometallics 24, 3219 (2005)

    Article  Google Scholar 

  26. D. Möhring, M. Nieger, B. Lewall, K.H. Dötz, Eur. J. Org. Chem. 12, 2620 (2005)

    Article  Google Scholar 

  27. B. Jacques, M. Chavarot, F. Rose-Munch, E. Rose, Angew. Chem. Int. Ed. 45, 3481 (2006)

    Google Scholar 

  28. F. Eloi, D.Jonathan Rose-Munch, J.-P. Tranchier, E. Rose, Organometallics 25, 4554 (2006)

    Article  CAS  Google Scholar 

  29. D. Cetiner, J.-P. Tranchier, F. Rose-Munch, E. Rose, P. Herson, Organometallics 27, 784 (2008)

    Article  CAS  Google Scholar 

  30. L.V. Dinh, C.S. Consorti, C. Emnet, L.A. Gladyzs, Organometallics 25, 1245 (2006)

    Article  CAS  Google Scholar 

  31. M.-E. Moret, A.B. Chaplin, A.F. Lawrence, R. Scopelliti, P.J. Dyson, Organometallics 24, 4039 (2005)

    Article  CAS  Google Scholar 

  32. T.T. To, E.J. Heilweil, C.B. Duke III, K.R. Ruddick, C.E. Webster, T.J. Burkey, J. Phys. Chem. A 113, 2666 (2009)

    Article  CAS  Google Scholar 

  33. J.A. Heppert, M.A. Morgenstern, D.M. Scherubel, F. Takusagawa, M.R. Shaker, Organometallics 7, 1715 (1988)

    Article  CAS  Google Scholar 

  34. S. Lotz, P.H. van Rooyen, R. Meyer, Adv. Organomet. Chem. 37, 219 (1995)

    CAS  Google Scholar 

  35. Berger, J.P. Djukic, C. Michon, Coord. Chem. Rev. 225, 215 (2002)

    Article  CAS  Google Scholar 

  36. J.A. Heppert, M.E. Thomas-Miller, D.M. Scherubel, F. Takusagawa, M.M. Morgenstern, M.R. Shaker, Organometallics 8, 1199 (1989)

    Article  CAS  Google Scholar 

  37. P.H. van Rooyen, M. Schindehutte, S. Lotz, Organometallics 11, 1104 (1992)

    Article  Google Scholar 

  38. S. Lotz, M. Schindehutte, P.H. van Rooyen, Organometallics 11, 629 (1992)

    Article  CAS  Google Scholar 

  39. J.D. Jackson, S.J. Villa, D.S. Bacon, R.D. Pike, Organometallics 13, 3972 (1994)

    Article  CAS  Google Scholar 

  40. W. Beck, B. Niemer, B. Wagner, Angew. Chem. Int. Ed. 28, 1705 (1989)

    Google Scholar 

  41. S. Lotz, N. Harris, Unpublished results (2013)

  42. S.G. Davies, T.J. Donohoe, Synlett 5, 323 (1993)

    Article  Google Scholar 

  43. Pfletschinger, T.K. Dargel, J.W. Bats, H.-G. Schmalz, W. Koch, Chem. Eur. J. 5, 537 (1999)

    Article  CAS  Google Scholar 

  44. D.W. Clack, L.A.P. Kane-Maguire, J. Organomet. Chem. 145, 201 (1978)

    Article  CAS  Google Scholar 

  45. C.A. Merlic, J.C. Walsh, D.J. Tantillo, K.N. Houk, J. Am. Chem. Soc. 121, 3596 (1999)

    Article  CAS  Google Scholar 

  46. D.J. Tantillo, B.N. Hietbrink, C.A. Merlic, K.N. Houk, J. Am. Chem. Soc. 123, 5851 (2001)

    Article  CAS  Google Scholar 

  47. C. Scheeren, F. Maasarani, A. Hijazi, J.P. Djukic, M. Pfeffer, S.D. Zaric, X.-F. Le Goff, L. Ricard, Organometallics 26, 3336 (2007)

    Article  CAS  Google Scholar 

  48. Hijazi, J.P. Djukic, M. Pfeffer, L. Ricard, N. Kyritsakas-Gruber, J. Raya, P. Bertani, A. de Cian, Inorg. Chem. 45, 4589 (2006)

    Article  CAS  Google Scholar 

  49. Hijazi, J.P. Djukic, L. Allouche, A. de Cian, M. Pfeffer, S.D. Zaric, A.F. Le Goff, L. Ricard, Organometallics 26, 4180 (2007)

    Article  CAS  Google Scholar 

  50. J.P. Djukic, C. Boulho, D. Sredojevic, C. Scheeren, S. Zaric, L. Ricard, M. Pfeffer, Chem. Eur. J. 15, 10830 (2009)

    Article  CAS  Google Scholar 

  51. J.P. Djukic, A. Berger, M. Duquenne, M. Pfeffer, A. de Cian, N. Kyritsakas-Gruber, Organometallics 23, 5757 (2004)

    Article  CAS  Google Scholar 

  52. J.P. Djukic, W. Iali, M. Pfeffer, X.F. Le Goff, Chem. Commun. 47, 3631 (2011)

    Article  CAS  Google Scholar 

  53. J.P. Djukic, A. Maisse, M. Pfeffer, K.H. Dötz, M. Nieger, Eur. J. Inorg. Chem. (11), 1781 (1998)

  54. J.P. Djukic, A. Maisse-Francoise, M. Pfeffer, K.H. Dötz, A. De Cian, J. Fischer, Organometallics 19, 5484 (2000)

    Article  CAS  Google Scholar 

  55. J.P. Djukic, C. Michon, A. Berger, M. Pfeffer, A. de Cian, N. Kyritsakas-Gruber, J. Organomet. Chem. 691, 846 (2006)

    Article  CAS  Google Scholar 

  56. E.L.S. Gomes, M. Horner, V.G. Young Jr, J. Dupont, V. Caliman, O.L. Casagrande Jr, Organometallics 18, 3898 (1999)

    Article  CAS  Google Scholar 

  57. O.L. Casagrande Jr., E.L.S. Gomes, J. Dupont, R. Burrow, A.J. Lough, J. Chem. Soc., Dalton Trans. (10), 1634 (2001)

  58. E.L.S. Gomes, O.L. Casagrande Jr, Polyhedron 28, 1127 (2009)

    Article  CAS  Google Scholar 

  59. J.D. Offner, G. Schnakenburg, F. Rose-Munch, E. Rose, K.H. Dötz, Organometallics 29, 3308 (2010)

    Article  Google Scholar 

  60. J.D. Offner, G. Schankenburg, F. Rose-Munch, E. Rose, K.H. Dötz, Inorg. Chem. 50, 5183 (2011)

    Article  Google Scholar 

  61. M. Zora, E.U. Gungor, Tetrahedron Lett. 42, 4733 (2001)

    Article  CAS  Google Scholar 

  62. K.S. Chan, H. Zhang, Synth. Commun. 25, 635 (1995)

    Article  CAS  Google Scholar 

  63. J. Bennewitz, M. Nieger, B. Lewall, K.H. Dötz, J. Organomet. Chem. 690, 5892 (2005)

    Article  CAS  Google Scholar 

  64. D.I. Bezuidenhout, S. Lotz, D.C. Liles, B. van der Westhuizen, Coord. Chem. Rev. 256, 479 (2012)

    Article  CAS  Google Scholar 

  65. M.A. Sierra, Chem. Rev. 100, 3591 (2000)

    Article  CAS  Google Scholar 

  66. D.I. Bezuidenhout, E. van der Watt, D.C. Liles, M. Landman, S. Lotz, Organometallics 27, 2447 (2008)

    Article  CAS  Google Scholar 

  67. D.I. Bezuidenhout, W. Barnard, B. van der Westhuizen, E. van der Watt, D.C. Liles, Dalton Trans. 40, 6711 (2011)

    Article  CAS  Google Scholar 

  68. D.I. Bezuidenhout, S. Lotz, M. Landman, D.C. Liles, Inorg. Chem. 50, 1521 (2011)

    Article  CAS  Google Scholar 

  69. M. Landman, T. Isenburg, P.H. van Rooyen, S. Lotz, Inorg. Chim. Acta 310, 147 (2000)

    Article  CAS  Google Scholar 

  70. H. Li, G.B. Carpenter, D.A. Sweigart, Organometallics 19, 1823 (2000)

    Article  CAS  Google Scholar 

  71. K. Yu, H. Li, E.J. Watson, K.L. Virkaitis, G.B. Carpenter, D.A. Sweigart, Organometallics 20, 3550 (2001)

    Article  CAS  Google Scholar 

  72. X. Zhang, C.A. Dullaghan, E.J. Watson, G.B. Carpenter, D.A. Sweigart, Organometallics 17, 2067 (1998)

    Article  CAS  Google Scholar 

  73. H. Li, K. Yu, E.J. Watson, K.L. Virkaitis, J.S. D’Acchioli, G.B. Carpenter, D.A. Sweigart, P.T. Czech, K.R. Overly, F. Coughlin, Organometallics 21, 1262 (2002)

    Article  CAS  Google Scholar 

  74. X. Zhang, C.A. Dullaghan, G.B. Carpenter, D.A. Sweigart, Q. Meng, Chem. Commun. (1), 93 (1998)

  75. X. Zhang, G.B. Carpenter, D.A. Sweigart, Organometallics 18, 4887 (1999)

    Article  CAS  Google Scholar 

  76. N. Vinokurov, J.R. Garabatos-Perera, Z. Zhao-Karger, M. Wiebcke, H. Butenschön, Organometallics 27, 1878 (2008)

    Article  CAS  Google Scholar 

  77. V. Dufaud, J. Thivolle-Cazat, J.-M. Basset, R. Mathieu, J. Jaud, J. Waissermann, Organometallics 10, 4005 (1991)

    Article  CAS  Google Scholar 

  78. D. Prim, Tetrahedron 60, 3325 (2004)

    Article  CAS  Google Scholar 

  79. G.I. McGrew, C. Stanciu, J. Zhang, P.J. Carrol, S.D. Dreher, P.J. Walsh, Angew. Chem. Int. Ed. 51, 11510 (2012)

    Article  CAS  Google Scholar 

  80. G.I. McGrew, J. Temaismithi, P.J. Carroll, P.J. Walsh, Angew. Chem. Int. Ed. 122, 5673 (2010)

    Article  Google Scholar 

  81. J. Zhang, C. Stanciu, B. Wang, M.M. Hussain, C.-S. Da, P.J. Carroll, S.D. Dreher, P.J. Walsh, J. Am. Chem. Soc. 133, 20552 (2011)

    Article  CAS  Google Scholar 

  82. Auffrant, D. Prim, F. Rose-Munch, E. Rose, J. Vaissermann, Organometallics 20, 3214 (2001)

    Article  CAS  Google Scholar 

  83. Auffrant, D. Prim, F. Rose-Munch, E. Rose, J. Vaissermann, Organometallics 21, 3500 (2002)

    Article  CAS  Google Scholar 

  84. Jacques, J.-P. Tranchier, F. Rose-Munch, E. Rose, G.R. Stephenson, C. Guyard-Duhayon, Organometallics 23, 184 (2004)

    Article  CAS  Google Scholar 

  85. S. Sun, L.K. Yeung, D.A. Sweigart, T.-Y. Lee, S.S. Lee, Y.K. Chung, S.R. Switzer, R.D. Pike, Organometallics 14, 2613 (1995)

    Article  CAS  Google Scholar 

  86. S. Sun, C.A. Dullaghan, G.B. Carpenter, A.L. Rieger, P.H. Rieger, D.A. Sweigart, Angew. Chem. Int. Ed. Engl. 34, 2540 (1995)

    Article  CAS  Google Scholar 

  87. J.A. Rheingold, K.L. Virkaitis, G.B. Carpenter, S. Sun, D.A. Sweigart, P.T. Czech, K.R. Overly, J. Am. Chem. Soc. 127, 11146 (2005)

    Article  Google Scholar 

  88. E.J. Watson, K.L. Virkaitis, H. Li, A.J. Nowak, J.S. D’Acchioli, K. Yu, G.B. Carpenter, Y.K. Chung, D.A. Sweigart, Chem. Commun. (5), 457 (2001)

  89. W. Dai, S. Bok Kim, R.D. Pike, C.L. Cahill, D.A. Sweigart, Organometallics 29, 5173 (2010)

    Article  CAS  Google Scholar 

  90. L. Shao, S.J. Geib, N.J. Cooper, Organometallics 22, 4361 (2003)

    Article  CAS  Google Scholar 

  91. J.P. Berger, C. Djukic, Michon. Coord. Chem. Rev. 225, 215 (2002)

    Article  CAS  Google Scholar 

  92. J.A. Reingold, S.U.K. Son, G.B. Carpenter, D.A. Sweigart, J. Inorg. Organomet. Polym. Mat. 16, 1 (2006)

    Article  CAS  Google Scholar 

  93. M. Oh, J.A. Reingold, G.B. Carpenter, D.A. Sweigart, J. Organomet. Chem. 687, 78 (2003)

    Article  CAS  Google Scholar 

  94. M. Oh, G.B. Carpenter, D.A. Sweigart, Angew. Chem. Int. Ed. 41, 3650 (2002)

    Article  CAS  Google Scholar 

  95. S.B. Kim, C. Cai, S. Sun, D.A. Sweigart, Angew. Chem. Int. Ed. 48, 2907 (2009)

    Article  CAS  Google Scholar 

  96. S.B. Kim, C. Cai, J. Kim, S. Sun, D.A. Sweigart, Organometallics 28, 5341 (2009)

    Article  CAS  Google Scholar 

  97. S.B. Kim, R.D. Pike, D.A. Sweigart, Acc. Chem. Res. (2013). doi:10.1021/ar300353n

    Google Scholar 

  98. E.O. Fischer, K. Öfele, H. Essler, W. Fröhlich, J.P. Mortensen, W. Semmlinger, Chem. Ber. 91, 2763 (1958)

    Article  CAS  Google Scholar 

  99. B. Murugesapandian, P.W. Roesky, Z. Anorg. Allg. Chem. 637, 1818 (2011)

    Article  CAS  Google Scholar 

  100. B. Murugesapandian, P.W. Roesky, Eur. J. Inorg. Chem. (2), 292 (2012)

  101. B. Murugesapandian, P.W. Roesky, Inorg. Chem. 50, 1698 (2011)

    Google Scholar 

  102. B. Murugesapandian, P.W. Roesky, Eur. J. Inorg. Chem. (26), 4103 (2011)

  103. S.S. Kaye, J.R. Long, J. Am. Chem. Soc. 130, 806 (2008)

    Article  CAS  Google Scholar 

  104. M.E. Wright, J. Organomet. Chem. 376, 353 (1989)

    Article  CAS  Google Scholar 

  105. H. Schumann, A.M. Arif, T.G. Richmond, Polyhedron 9, 1677 (1990)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

SL and DIB are grateful to Dwight Sweigart who was an exceptional mentor, enthusiastic collaborator and dear friend. SL acknowledges Fulbright for financial support in 2006/7 during a sabbatical at Brown University and thanks the NRF for financial support under Grant No. 73679.

Author information

Authors and Affiliations

  1. Chemistry Department, University of Pretoria, Private Bag X20, Hatfield, Pretoria, 0028, South Africa

    Daniela I. Bezuidenhout, Belinda van der Westhuizen, Nina A. van Jaarsveld & Simon Lotz

Authors
  1. Daniela I. Bezuidenhout
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Belinda van der Westhuizen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nina A. van Jaarsveld
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Simon Lotz
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Simon Lotz.

Additional information

The authors dedicate this paper to the memory of Prof. Dwight A. Sweigart.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bezuidenhout, D.I., van der Westhuizen, B., van Jaarsveld, N.A. et al. Trends in the chemistry of mono- to multimetal π-arene complexes of chromium and manganese. J Inorg Organomet Polym 24, 39–57 (2014). https://doi.org/10.1007/s10904-013-9983-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-013-9983-x

Keywords

Search

Navigation