Skip to main content
SpringerLink
Log in
Book cover

The Privileged Pincer-Metal Platform: Coordination Chemistry & Applications pp 239–268Cite as

Recent Advances on the Chemistry of POCOP–Nickel Pincer Compounds

  • Chapter
  • First Online:

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 54))

Abstract

A description of the vertiginous development of the chemistry of POCOP–Ni complexes and their applications is described. Recent advances include the discovery and initially challenging synthesis of these species to the high-yield green procedures recently developed. The various applications of these compounds, particularly in catalysis, are discussed in detail.

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

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  1. Morales-Morales D, Jensen CM (2007) The chemistry of pincer compounds. Elsevier, Amsterdam

    Google Scholar 

  2. van Koten G, Milstein D (eds) (2013) Organometallic pincer chemistry, vol 40, Topics in organometallic chemistry. Springer, Heidelberg

    Google Scholar 

  3. Chase PA, van Koten G (2010) The pincer ligand: its chemistry and applications (catalytic science), 1st edn. Imperial College, London

    Google Scholar 

  4. van der Boom ME, Milstein D (2003) Chem Rev 103:1759

    Article  Google Scholar 

  5. Jensen CM (1999) Chem Commun 2443–2449

    Google Scholar 

  6. van Koten G (1989) Pure Appl Chem 61:1681

    Google Scholar 

  7. Goldberg KI, Goldman AS (eds) (2004) Activation and functionalization of C–H bonds, vol 885, ACS symposium series. American Chemical Society, Washington, DC

    Google Scholar 

  8. Morales-Morales D (2009) Iridium-mediated alkane dehydrogenation. In: Oro LA, Claver C (eds) Iridium complexes in organic synthesis, 1st edn. Wiley-VCH, Weinheim, ch 13

    Google Scholar 

  9. Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Chem Rev 111:1761

    Article  CAS  Google Scholar 

  10. Haibach MC, Kundu S, Brookhart M, Goldman AS (2012) Acc Chem Res 45:947

    Article  CAS  Google Scholar 

  11. Szabo JK, Wendt OF (eds) (2014) Pincer and pincer-type complexes: applications in organic synthesis and catalysis, 1st edn. Wiley-VCH, Weinheim

    Google Scholar 

  12. Albrecht M, Morales-Morales D (2009) Pincer-type iridium complexes for organic transformations. In: Oro LA, Claver C (eds) Iridium complexes in organic synthesis, 1st edn. Wiley-VCH, Weinheim, Chap 12

    Google Scholar 

  13. Morales-Morales D (2004) Rev Soc Quim Mex 48:338

    CAS  Google Scholar 

  14. Serrano-Becerra JM, Morales-Morales D (2009) Curr Org Synth 6:169

    Article  CAS  Google Scholar 

  15. Singleton JT (2003) Tetrahedron 59:1837

    Article  CAS  Google Scholar 

  16. Selander N, Szabo KJ (2011) Chem Rev 111:2048

    Article  CAS  Google Scholar 

  17. Dupont J, Consorti CS, Spencer J (2005) Chem Rev 105:2527

    Article  CAS  Google Scholar 

  18. Jensen CM, Sun D, Lewandowski B, Kumashiro KK, Niemczura WP, Morales-Morales D, Wang Z (2001) In: Proceedings of the 2001 U.S. DOE hydrogen program review; National Renewable Energy Laboratory, Golden, CO, p 2500

    Google Scholar 

  19. Luca OR, Blakemore JD, Konezny SJ, Praetorius JM, Schmeier TJ, Hunsinger GB, Batista VS, Brudvig GW, Hazari N, Crabtree RH (2012) Inorg Chem 51:8704

    Article  CAS  Google Scholar 

  20. Torres-Nieto J, Garcia JJ (2007) Desulfurization catalyzed by nickel PCP-pincer compounds. In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier, Oxford, Chap 4

    Google Scholar 

  21. Bauer G, Kirchner KA (2011) Angew Chem Int Ed 50:5798

    Article  CAS  Google Scholar 

  22. Bhattacharya P, Guan H (2011) Comment Inorg Chem 32:88

    Article  CAS  Google Scholar 

  23. Wang Z-X, Liu N (2012) Eur J Inorg Chem 901

    Google Scholar 

  24. Campora J, Melero C (2004) The role of redox processes in reactions catalyzed by nickel and palladium complexes with anionic pincer ligands. In: Szabo JK, Wendt OF (eds) Pincer and pincer-type complexes: applications in organic synthesis and catalysis, 1st edn. Wiley-VCH, Weinheim, Chap 2

    Google Scholar 

  25. Adhikary A, Guan H (2014) Nickel-catalysed cross-coupling reactions. In: Szabo JK, Wendt OF (eds) (2014) Pincer and pincer-type complexes: applications in organic synthesis and catalysis, 1st edn. Wiley-VCH, Weinheim, Chap 5

    Google Scholar 

  26. Zargarian D, Castonguay A, Spasyuk DM (2013) Top Organomet Chem 40:131

    CAS  Google Scholar 

  27. Gómez-Benítez V, Baldovino-Pantaleón O, Herrera-Álvarez C, Toscano RA, Morales-Morales D (2006) Tetrahedron Lett 47:5059

    Article  Google Scholar 

  28. Shaw BL, Moulton CJ (1976) J Chem Soc Dalton Trans 1020

    Google Scholar 

  29. Albrecht M, van Koten G (2001) Angew Chem Int Ed 40:3750

    Article  CAS  Google Scholar 

  30. Morales-Morales D, Redón R, Yung C, Jensen CM (2000) Chem Commun 1619

    Google Scholar 

  31. Morales-Morales D, Cramer RE, Jensen CM (2002) J Organomet Chem 654:44

    Article  CAS  Google Scholar 

  32. Morales-Morales D (2008) Mini Rev Org Chem 5:141

    Article  CAS  Google Scholar 

  33. Hahn FE, Jahnke MC, Gómez-Benítez V, Morales-Morales D, Pape T (2005) Organometallics 24:6458

    Article  CAS  Google Scholar 

  34. Baldovino-Pantaleón O, Hernández-Ortega S, Morales-Morales D (2006) Adv Synth Catal 348:236

    Article  Google Scholar 

  35. Basauri-Molina M, Hernández-Ortega S, Morales-Morales D (2014) Eur J Inorg Chem 4619

    Google Scholar 

  36. Gómez-Benítez V, Hernández-Ortega S, Toscano RA, Morales-Morales D (2007) Inorg Chim Acta 360:2128

    Article  Google Scholar 

  37. Avila-Sorrosa A, Estudiante-Negrete F, Hernández-Ortega S, Toscano RA, Morales-Morales D (2010) Inorg Chim Acta 363:1262

    Article  CAS  Google Scholar 

  38. Baldovino-Pantaleón O, Hernández-Ortega S, Morales-Morales D (2005) Inorg Chem Commun 8:955

    Article  Google Scholar 

  39. Naghipour A, Sabounchei SJ, Morales-Morales D, Canseco-González D, Jensen CM (2007) Polyhedron 26:1445

    Article  CAS  Google Scholar 

  40. Ramírez-Rave S, Estudiante-Negrete F, Toscano RA, Hernández-Ortega S, Morales-Morales D, Grévy J-M (2014) J Organomet Chem 749:287

    Article  Google Scholar 

  41. Crisóstomo-Lucas C, Toscano RA, Morales-Morales D (2014) Tetrahedron Lett 55:5841

    Article  Google Scholar 

  42. Serrano-Becerra JM, Hernández-Ortega S, Morales-Morales D (2010) Inorg Chim Acta 363:1306

    Article  CAS  Google Scholar 

  43. Brayton DF, Beaumont PR, Fukushima EY, Sartain HT, Morales-Morales D, Jensen CM (2014) Organometallics 33:5198

    Article  CAS  Google Scholar 

  44. Morales-Morales D, Grause C, Kasaoka K, Redón R, Cramer RE, Jensen CM (2000) Inorg Chim Acta 958:300–302

    Google Scholar 

  45. Bedford RB, Draper SM, Scully PN, Welch SL (2000) New J Chem 24:745

    Article  CAS  Google Scholar 

  46. Morales-Morales D, Redon R, Yung C, Jensen CM (2004) Inorg Chim Acta 357:2953

    Article  CAS  Google Scholar 

  47. Göttker-Schnetmann I, White P, Brookhart M (2004) J Am Chem Soc 126:1804

    Article  Google Scholar 

  48. Salem H, Ben-David Y, Shimon LJW, Milstein D (2006) Organometallics 25:2292

    Article  CAS  Google Scholar 

  49. Cerón-Camacho R, Gómez-Benítez V, Le Lagadec R, Morales-Morales D, Toscano RA (2006) J Mol Catal A 247:124

    Article  Google Scholar 

  50. Bedford RB, Betham M, Blake ME, Coles SJ, Draper SM, Hursthouse MB, Scully PN (2006) Inorg Chim Acta 359:1870

    Article  CAS  Google Scholar 

  51. Wang Z, Sugiarti S, Morales CM, Jensen CM, Morales-Morales D (2006) Inorg Chim Acta 359:1923

    Article  CAS  Google Scholar 

  52. Pandarus V, Zargarian D (2007) Chem Commun 978

    Google Scholar 

  53. Vabre B, Lindeperg F, Zargarian D (2013) Green Chem 15:3188

    Article  CAS  Google Scholar 

  54. Zhang J, Medley CHM, Krause JA, Guan H (2010) Organometallics 29:6393

    Article  CAS  Google Scholar 

  55. Chakraborty S, Patel YJ, Krause JA, Guan H (2012) Polyhedron 32:30

    Article  CAS  Google Scholar 

  56. García-Eleno MA, Padilla-Mata E, Estudiante-Negrete F, Pichal-Cerda F, Hernández-Ortega S, Toscano RA, Morales-Morales D (2015) New J Chem 39:3361

    Article  Google Scholar 

  57. Kimura T, Uozumi Y (2006) Organometallics 25:4883

    Article  CAS  Google Scholar 

  58. Ananthnag GS, Mague JT, Balakrishna MJ (2015) Dalton Trans 44:3785

    Article  CAS  Google Scholar 

  59. Gallego D, Brück A, Irran E, Meier F, Kaupp M, Driess M, Hartwig JF (2013) J Am Chem Soc 135:15617

    Article  CAS  Google Scholar 

  60. Salah AB, Zargarian D (2011) Dalton Trans 40:8977

    Article  CAS  Google Scholar 

  61. Lefèvre X, Spasyuk DM, Zargarian D (2011) J Organomet Chem 696:864

    Article  Google Scholar 

  62. Zargarian D, Salah AB (2011) Acta Crystallogr E67:m940

    Google Scholar 

  63. Salah AB, Zargarian D (2011) Acta Crystallogr E67:m437

    Google Scholar 

  64. Vabre B, Spasyuk DM, Zargarian D (2012) Organometallics 31:8561

    Article  CAS  Google Scholar 

  65. Hao J, Vabre B, Zargarian D (2014) Organometallics 33:6568

    Article  CAS  Google Scholar 

  66. Wilson GLO, Abraha M, Krause JA, Guan H (2015) Dalton Trans. doi:10.1039/c5dt00161g

  67. Kwan M-L, Conry SJ, Carfagna CHS, Press LP, Ozerov OV, Hoffman NW, Sykora RE (2012) Acta Crystallogr E68:m1282

    Google Scholar 

  68. Salah A, Corpet M, Khan NU-H, Zargarian D, Spasyuk D (2015) New J Chem. doi:10.1039/C5NJ00807G

  69. Farrington EJ, Martinez EV, Williams BS, van Koten G, Brown JM (2002) Chem Commun 308

    Google Scholar 

  70. Koridze AA, Kuklin SA, Sheloumov AM, Dolgushin FM, Lagunova VY, Petukhova II, Ezerniskaya MG, Peregudov AS, Petrovskii PV, Vorontsov EV, Baya M, Poli R (2004) Organometallics 23:4585

    Article  CAS  Google Scholar 

  71. Kuklin SA, Sheloumov AM, Dolgushin FM, Ezerniskaya MG, Peregudov AS, Petrovskii PV, Koridze AA (2006) Organometallics 25:5466

    Article  CAS  Google Scholar 

  72. Koridze AA, Sheloumov AM, Kuklin SA, Lagunova VY, Petukhova II, Dolgushin FM, Ezerniskaya MG, Peregudov AS, Petrovskii PV, Macharashvili AA, Chedia RV (2002) Russ Chem Bull Int Ed 51:1077

    Article  CAS  Google Scholar 

  73. Koridze AA, Polezhaev AV, Safronov SV, Sheloumov AM, Dolgushin FM, Ezernitskaya MG, Lokshin BV, Petrovskii PV, Peregudov AS (2010) Organometallics 29:4360

    Article  CAS  Google Scholar 

  74. Bonnet S, Lutz M, Spek AL, van Koten G, Gebbink RJM (2008) Organometallics 27:159

    Article  CAS  Google Scholar 

  75. Bonnet S, Li J, Siegler MA, von Chrzanowski LS, van Koten G, Gebbink RJMK (2009) Chem Eur J 15:3340

    Article  CAS  Google Scholar 

  76. Bonnet S, van Lenthe JH, Siegler MA, Spek AL, van Koten G, Gebbink RJMK (2009) Organometallics 28:2325

    Article  CAS  Google Scholar 

  77. Bonnet S, Lutz M, Spek AL, van Koten G, Gebbink RJMK (2010) Organometallics 29:1157

    Article  CAS  Google Scholar 

  78. Bonnet S, Siegler MA, van Lenthe JH, Lutz M, Spek AL, van Koten G, Gebbink RJMK (2010) Eur J Inorg Chem 4667

    Google Scholar 

  79. Walter MC, White PS (2011) New J Chem 35:1842

    Article  CAS  Google Scholar 

  80. Espinosa-Jalapa NA, Hernández-Ortega S, Morales-Morales D, Le Lagadec R (2012) J Organomet Chem 716:103

    Article  CAS  Google Scholar 

  81. Estudiante-Negrete F, Hernández-Ortega S, Morales-Morales D (2012) Inorg Chim Acta 387:58

    Article  CAS  Google Scholar 

  82. Espinosa-Jalapa NA, Hernández-Ortega S, Le Goff X-F, Morales-Morales D, Djukic J-P, Le Lagadec R (2013) Organometallics 32:2661

    Article  CAS  Google Scholar 

  83. Zhang J, Adhikary A, King KM, Krause JA, Guan H (2012) Dalton Trans 41:7959

    Article  CAS  Google Scholar 

  84. Lindsley CW (2013) ACS Chem Neurosci 4:905

    Article  CAS  Google Scholar 

  85. Lawrence SA (2004) Amines: synthesis properties and applications. Cambridge University, Cambridge

    Google Scholar 

  86. Yim JCH, Schafer LL (2014) Eur J Org Chem 6825

    Google Scholar 

  87. Huang L, Arndt M, Gooßen K, Heydt H, Gooßen LJ (2015) Chem Rev 115:2596

    Article  CAS  Google Scholar 

  88. Bernoud E, Lepori C, Mellah M, Schulzab E, Hannedouche J (2015) Catal Sci Technol 5:2017

    Article  CAS  Google Scholar 

  89. Pandarus V, Zargarian D (2007) Organometallics 26:4321

    Article  CAS  Google Scholar 

  90. Castonguay A, Spasyuk DM, Madern N, Beauchamp AL, Zargarian D (2009) Organometallics 28:2134

    Article  CAS  Google Scholar 

  91. Lefèvre X, Durieux G, Lesturgez S, Zargarian D (2011) J Mol Catal A Chem 335:1

    Article  Google Scholar 

  92. Salah AB, Offenstein C, Zargarian D (2011) Organometallics 30:5352

    Article  CAS  Google Scholar 

  93. Chakraborty S, Krause JA, Guan H (2009) Organometallics 28:582

    Article  CAS  Google Scholar 

  94. Chakraborty S, Zhang J, Krause JA, Guan H (2010) J Am Chem Soc 132:8872

    Article  CAS  Google Scholar 

  95. Huang F, Zhang CH, Jiang J, Wang Z-X, Guan H (2011) Inorg Chem 50:3816

    Article  CAS  Google Scholar 

  96. Wang L, Guo J, Wen J, He H, Zhang J (2013) Eur Phys J D 67:241

    Article  Google Scholar 

  97. Chakraborty S, Zhang J, Patel YJ, Krause JA, Guan H (2013) Inorg Chem 52:37

    Article  CAS  Google Scholar 

  98. Corey EJ, Wu YJ (1993) J Am Chem Soc 115:8871

    Article  CAS  Google Scholar 

  99. Fleming FF, Shook BC (2002) Tetrahedron 58:1

    Article  CAS  Google Scholar 

  100. Fukuda Y, Okamoto Y (2002) Tetrahedron 58:2513

    Article  CAS  Google Scholar 

  101. Fan Y-CH, Du GF, Sun W-F, Kang W, Kang W, He L (2012) Tetrahedron Lett 53:2231

    Article  CAS  Google Scholar 

  102. Chakraborty S, Patel YJ, Krause JA, Guan H (2013) Angew Chem Int Ed 52:7523

    Article  CAS  Google Scholar 

  103. Xu G, Li X, Sun H (2011) J Organomet Chem 696:3011

    Article  CAS  Google Scholar 

  104. Chen T, Yang L, Li L, Huang K-W (2012) Tetrahedron 68:6152

    Article  CAS  Google Scholar 

  105. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    Article  CAS  Google Scholar 

  106. Solano-Prado MA, Estudiante-Negrete F, Morales-Morales D (2010) Polyhedron 29:592

    Article  CAS  Google Scholar 

  107. Vabre B, Petiot P, Declercq R, Zargarian D (2014) Organometallics 33:5173

    Article  CAS  Google Scholar 

Download references

Acknowledgments

M. A. thanks the UNAM IQ for support. D. M-M. gratefully acknowledges the support and enthusiasm of former and current group members and colleagues. The research from our group described in this paper is supported by CONACYT and PAPIIT-DGAPA-UNAM.

Author information

Authors and Affiliations

  1. Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, 04510, Mexico, Mexico

    Matthew Asay & David Morales-Morales

Authors
  1. Matthew Asay
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. David Morales-Morales
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to David Morales-Morales .

Editor information

Editors and Affiliations

  1. Organic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Utrecht, The Netherlands

    Gerard van Koten

  2. Department of Chemistry & Biology, Ryerson University, Toronto, Canada

    Robert A Gossage

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Asay, M., Morales-Morales, D. (2015). Recent Advances on the Chemistry of POCOP–Nickel Pincer Compounds. In: van Koten, G., Gossage, R. (eds) The Privileged Pincer-Metal Platform: Coordination Chemistry & Applications. Topics in Organometallic Chemistry, vol 54. Springer, Cham. https://doi.org/10.1007/3418_2015_135

Download citation

Publish with us

Policies and ethics

Search

Navigation