ECE-type pincer complexes of nickel

Topics in Organometallic Chemistry

Volumn 40, Issue , 2013, Pages 131-174

  Zargarian, Davit ^a   Castonguay, Annie ^a   Spasyuk, Denis M ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

NCN; PCP; Pincer complexes of nickel; PNCN; PNCNP; POCN; POCOP; SCS

Indexed keywords

EID: 84868514070     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-642-31081-2_5     Document Type: Review

References (108)

1. Moutlon CJ, Shaw BL (1976) Transition metal-carbon bonds. Part XLII. Complexes of nickel, palladium, platinum, rhodium and iridium with the tridentate ligand 2,6-bis[(di-tbutylphosphino) methyl]phenyl. Dalton Trans 1020-1024
2. van Koten G, Jastrzebski JTBH, Noltes JG, Spek AL, Schoone JC (1978) Triorganotin cations stabilized by intramolecular Sn-N coordination; synthesis and characterization of {C, N, N0-2,6-bis[(dimethylamino)methyl]phenyl} diorganotin bromides. J Organomet Chem 148:233-245
3. van Koten G, Timmer K, Noltes JG, Spek AL (1978) A novel type of Pt-C interaction and a model for the final stage in reductive elimination processes involving C-C coupling at Pt; synthesis and molecular geometry of [l,N,N0-q-2,6-bis((dimethylamino)methyl}-toluene] iodoplatinum(II) Tetrafluoroborate. J Chem Soc Chem Commun 250-252
4. Fryzuk MD, Montgomery CD (1989) Amides of the platinum group metal. Coord Chem Rev 95:1-40
5. Adhikari D, Huffman JC, Mindiola DJ (2007) Structural elucidation of a nickel boryl complex. A recyclable borylation Ni(II) reagent of bromobenzene. Chem Commun 4489-4491
6. Ozerov OV, Guo C, Fan L, Foxman BM (2004) Oxidative addition of NC and NH bonds to zerovalent nickel, palladium, and platinum. Organometallics 23:5573-5580
7. Csok Z, Vechorkin O, Harkins SB, Scopelliti R, Hu X (2008) Nickel complexes of a pincer NN2 ligand: multiple carbon-chloride activation of CH2Cl2 and CHCl3 leads to selective carbon-carbon bond formation. J Am Chem Soc 130:8156-8157
8. Ingleson MJ, Fullmer BC, Buschhorn DT, Fan H, Pink M, Huffman JC, Caulton KG (2008) Influence of the d-electron count on CO binding by three-coordinate [(tBu2PCH2SiMe2)2N] Fe, -Co, and -Ni. Inorg Chem 47:407-409
9. Liang L-C, Chien P-S, Huang Y-L (2006) Intermolecular arene C-H activation by nickel(II). J Am Chem Soc 128:15562-15563
10. Mitton SJ, McDonald R, Turculet L (2009) Nickel and palladium silyl pincer complexes: unusual structural rearrangements that involve reversible Si-C(sp3) and Si-C(sp2) bond activation. Angew Chem 121:8720-8723
11. Rozenel S, Kerr JB, Arnold J (2011) Metal complexes of Co, Ni and Cu with the pincer ligand HN(CH2CH2PiPr2)2: preparation, characterization and electrochemistry. Dalton Trans 40:10397-10405
12. van Koten G (1989) Tuning the reactivity of metals held in a rigid ligand environment. Pure Appl Chem 61:1681-1694
13. Gusev DG, Lough AJ (2002) Experimental and computational study of pincer complexes of ruthenium with Py, CO, and N2 ligands. Organometallics 21:5091-5099
14. Rimml H, Venanzi LM (1983) The facile cyclometallation reaction of 1,3-bis[(diphenylphosphino) methyl]benzene. J Organomet Chem 259:C6-C7
15. Johnson MT, Wendt OF (2011) Synthesis, characterisation and crystal structure of a novel nickel(II) phosphine complex, trans-[Ni2Cl4{cis-(Cy2PCH2) 2C6H4}2]. Inorganica Chim Acta 367:222-224
16. Rimml H, Venanzi LM (1984) A stable binuclear complex containing Pd-H-Pd bonds. J Organomet Chem 260:C52-C54
17. Kennedy AR, Cross RJ, Muir KW (1995) Preparation and crystal structure of trans-[NiBr {C6H3-2,6-(CH2PCy2)2}]. Inorganica Chim Acta 231:195-200
18. Huck WTS, Snellink-Ruel B, van Veggel FCJM, Reinhoudt DN (1997) New building blocks for the noncovalent assembly of homo-and hetero-multinuclear metallodendrimers. Organometallics 16:4287-4291
19. Bachechi F (2003) X-ray structural analysis of NiII, PdII, and PtII complexes with the potentially tridentate ligand 1,3- bis(diphenylphosphinomethyl)-benzene, 1,3-C6H4(CH2PPh2)2. Struct Chem 14:263-269
20. Kozhanov KA, Bubnov MP, Cherkasov VK, Abakumov GA (2006) EPR study of spinlabeled nickel NCN-pincer complexes. Dokl Chem 407:35-38
21. Kozhanov KA, Bubnov MP, Cherkasov VK, Fukin GK, Abakumov GA (2004) Dalton Trans 2957-2962
22. Kozhanov KA, Bubnov MP, Vavilina NN, Efremova LY, Fukin GK, Cherkasov VK, Abakumov GA (2009) Polyhedron 28:2555-2558
23. Starikov AG, Minyaev RM, Kozhanov KA, Bubnov MP, Cherkasov VK, Abakumov GA (2010) Russ Chem Bull Int Ed 59:1110-1115
24. Kozhanov KA, Bubnov MP, Cherkasov VK, Vavilina NN, Efremova LY, Artyushin OI, Odinet IL, Abakumov GA (2008) Dalton Trans 2849-2853
25. Kozhanov KA, Bubnov MP, Cherkasov VK, Fukin GK, Abakumov GA (2003) Chem Commun 2610-2611
26. Ca'mpora J, Palma P, del Río D, Álvarez E (2004) Organometallics 23:1652-1655
27. Ca'mpora J, Palma P, del Río D, Conejo MM, Álvarez E (2004) Organometallics 23:5653-5655
28. Castonguay A, Beauchamp AL, Zargarian D (2008) Organometallics 27:5723-5732
29. Boro BJ, Duesler EN, Goldberg KI, Kemp RA (2009) Inorg Chem 48:5081-5087
30. Boro BJ, Dickie DA, Goldberg KI, Kemp RA (2008) Acta Cryst E E64:m1304
31. Boro BJ, Dickie DA, Duesler EN, Goldberg KI, Kemp RA (2008) Acta Cryst E E64:m1402
32. Groux LF, Be'langer-Garie'py F, Zargarian D (2005) Can J Chem 83:634-639
33. Smith RC, Protasiewicz JD (2004) Organometallics 23:4215-4222
34. Ma L, Wobser SD, Protasiewicz JD (2007) J Organomet Chem 692:5331-5338
35. Ma L, Imbesi PM, Updegraff JB III, Hunter AD, Protasiewicz JD (2007) Inorg Chem 46:5220-5228
36. Lipke MC, Woloszynek RA, Ma L, Protasiewicz JD (2009) Organometallics 28:188-196
37. Schmeier TJ, Hazari N, Incarvitoa CD, Raskatovb JA (2011) Chem Commun 47:1824-1826
38. Levina VA, Rossin A, Belkova NV, Chierotti MR, Epstein LM, Filippov OA, Gobetto R, Gonsalvi L, Lledo's A, Shubina ES, Zanobini F, Peruzzini M (2011) Angew Chem Int Ed 50:1367-1370
39. Rossin A, Peruzzini M, Zanobini F (2011) Dalton Trans 40:4447-4452
40. van der Boom ME, Liou S-Y, Shimon LJW, Ben-David Y, Milstein D (2004) Inorganica Chim Acta 357:4015-4023
41. Castonguay A, Sui-Seng C, Zargarian D, Beauchamp AL (2006) Organometallics 25:602-608
42. Ess DH, Brigham Young University, Unpublished results communicated privately
43. Castonguay A, Charbonneau F, Beauchamp AL, Zargarian D (2005) {2,6-Bis [(dimethylamino)methyl]phenyl-2-N, C1, N0}-chloronickel(II). Acta Cryst E61: m2240-m2241
44. Castonguay A, Beauchamp AL, Zargarian D (2009) Inorg Chem 48:3177-3184
45. Castonguay A, Spasyuk DM, Madern N, Beauchamp AL, Zargarian D (2009) Organometallics 28:2134-2141
46. Albrecht M, van Koten G (2001) Platinum group organometallics based on pincer complexes: sensors, switches, and catalysts. Angew Chem Int Ed 40:3750-3781
47. Frey M (2002) Hydrogenases: hydrogen-activating enzymes. ChemBioChem 3:153-160
48. Grove DM, van Koten G, Zoet R (1983) Unique stable organometallic nickel(III) complexes: syntheses and the molecular structure of Ni[C6H3(CH2NMe2)-o, o0]I2. J Am Chem Soc 105:1379-1380
49. Grove DM, van Koten G, Ubbels HJC, Zoet R (1984) Organonickel(II) complexes of the terdentate monoanionic ligand o, o0-bis[(dimethylamino)methyl] phenyl(N-C-N). Syntheses and the X-ray crystal structure of the stable nickel(II) formate [Ni(N-C-N)O2CH]. Organometallics 3:1003-1009
50. Steenwinkel P, Gossage RA, van Koten G (1998) Recent findings in cyclometallation of meta-substituted aryl ligands by platinum group metal complexes by CAryl-R bond activation (RH, CR3, SiR3). Chem Eur J 4:759-762
51. Pandarus V, Castonguay A, Zargarian D (2008) Ni(II) complexes featuring non-metallated pincer-type ligands. Dalton Trans 4756-4761
52. Fossey JS, Richards CJ (2004) Synthesis and X-ray crystal structure analysis of the first nickel bisoxazoline pincer complex. J Organomet Chem 689:3056-3059
53. Mitsudo K, Imura T, Yamaguchi T, Tanaka H (2008) Preparation of a cationic bisoxazolinic nickel pincer catalyst and its applications to Michael addition and Mizoroki-Heck reaction. Tetrahedron Lett 49:7287-7289
54. Contel M, Stol M, Casado MA, van Klink GPM, Ellis DD, Spek AL, van Koten G (2002) A bis(ortho-amine)aryl-gold(I) compound as an efficient, nontoxic, arylating reagent. Organometallics 21:4556-4559
55. Grove DM, van Koten G, Mul P, Zoet R, van der Linden JGM, Legters J, Schmitz JEJ, Murrall NW, Welch AJ (1988) Syntheses and characterization of unique organometallic nickel(III) aryl species. ESR and electrochemical studies and the X-ray molecular study of square-pyramidal [Ni{C6H3(CH2NMe2)2-o, o'}I2]. Inorg Chem 27:2466-2473
56. Grove DM, van Koten G, Mul WP, van der Zeijden AH, Terheijden J (1986) Arylnickel(III) species containing NO3, NO2, and NCS ligands. ESR data and the X-ray crystal structure of hexacoordinate (pyridine)bis(isothiocyanato)-[o, o0-bis{(dimethylamino)methyl}phenyl] nickel(III). Organometallics 5:322-326
57. Kozhanov KA, Bubnov MP (2006) EPR study of spin-labeled nickel NCN-pincer complexes. Dokl Akad Nauk 407:49-52
58. Kozhanov KA, Bubnov MP, Cherkasov VK, Fukin GK, Vavilina NN, Efremova LY, Abakumov GA (2009) First structurally characterized mixed-halogen nickel(III) NCN-pincer complex. J Magn Res 197:36-39
59. Grove DM, van Koten G, Verschuuren AHM (1988) New homogeneous catalysts in the addition of polyhalogenoalkanes to olefins; organonickel(II) complexes [Ni {C6H3(CH2NMe2)2-o, o0}X] (XCl, Br, I). J Mol Catal 45:169-174
60. Grove DM, Verschuuren AHM, van Koten G (1989) The homogeneously catalysed addition reaction of polyhalogenoalkanes to olefins by divalent arylnickel complexes: comparative reactivity and some important mechanistic leads. J Organomet Chem 372:C1-C6
61. Sasson Y, Rempel GL (1975) Selective transfer hydrogenolysis of 1,1,1,3-tetrachloro to 1,1,3-trichloro compounds. Synthesis 448-450
62. Tsujui J, Sato K, Nagashima H (1981) Activation of polyhaloalkanes by palladium catalyst. Facile addition of polyhaloalkanes to olefins. Chem Lett 1169-1170
63. van de Kuil LA, Grove DM, Gossage RA, Zwikker JW, Jenneskens LW, Drenth W, van Koten G (1997) Mechanistic aspects of the Kharasch addition reaction catalyzed by organonickel(II) complexes containing the monoanionic terdentate aryldiamine ligand system [C6H2(CH2NMe2)2-2,6-R-4]-. Organometallics 16:4985-4994
64. van de Kuil LA, Veldhuizen YSJ, Grove DM, Zwikker JW, Jenneskens LW, Drenth W, Smeets WJJ, Spek AL, van Koten G (1994) Organonickel(II) complexes containing aryl ligands with chiral pyrrolidinyl ring systems; syntheses and use as homogeneous catalysts for the Kharasch addition reaction. Recl Trav Chim Pays-Bas 113:267-277
65. Granel C, Dubois Ph, Je'rôme R, Teyssié Ph (1996) Controlled radical polymerization of methacrylic monomers in the presence of a bis(ortho-chelated) arylnickel(II) complex and different activated alkyl halides. Macromolecules 29:8576-8582
66. Knapen JWJ, van der Made AW, de Wilde JC, van Leeuwen PWNM, Wijkens P, Grove DM, van Koten G (1994) Homogeneous catalysts based on silane dendrimers functionalized with arylnickel(II) complexes. Nature 372:659-663
67. Gossage RA, Jastrzebski TBH, van Ameijde J, Mulders SJE, Brouwer AJ, Liskamp RMJ, van Koten G (1999) Synthesis and catalytic application of amino acid based dendritic macromolecules. Tetrahedron Lett 40:1413-1416
68. Kleij AW, Gossage RA, Klein Gebbink RJM, Brinkmann N, Reijerse EJ, Kragl U, Lutz M, Spek AL, van Koten G (2000) A "dendritic effect" in homogeneous catalysis with carbosilane-supported arylnickel(II) catalysts: observation of active-site proximity effects in atom-transfer radical addition. J Am Chem Soc 122:12112-12124
69. Pathmamanoharan C, Wijkens P, Grove DM, Philipse AP (1996) Paramagnetic silica particles: synthesis and grafting of a silane coupling agent containing nickel ions onto colloidal silica particles. Langmuir 12:4372-4377
70. van de Kuil LA, Grove DM, Zwikker JW, Jenneskens LW, Drenth W, van Koten G (1994) New soluble polysiloxane polymers containing a pendant terdentate aryldiamine ligand substituent holding a highly catalytically active organometallic nickel(II) center. Chem Mater 6:1675-1683
71. Stol M, Snelders DJM, Godbole MD, Havenith RWA, Haddleton D, Clarkson G, Lutz M, Spek AL, van Klink GPM, van Koten G (2007) 2,6-Bis(oxazolinyl) phenylnickel(II) bromide and 2,6-bis(ketimine)phenylnickel(II) bromide: synthesis, structural features, and redox properties. Organometallics 26:3985-3994
72. Bugarin A, Connell BT (2008) Chiral nickel(II) and palladium(II) NCN-pincer complexes based on substituted benzene: synthesis, structure, and lewis acidity. Organometallics 27:4357-4369
73. Lee DH, Sungwon JH, Park S (2008) Bis(imino)aryl complex of nickel(II): N, C, N-pincer type complex, (2,6-(2,6-Et2PhNCH)2C6H3)NiBr. Bull Korean Chem Soc 29:187-190
74. Hurtado J, Ibanez A, Rojas R, Valderrama M, Frohlich R (2011) Organonickel(II) complexes with anionic tridentate 1,3-bis(azolylmethyl)phenyl ligands. synthesis, structural characterization and catalytic behavior. J Braz Chem Soc 22:1750-1757
75. Shao D-D, Niu J-L, Hao X-Q, Gong J-F, Song M-P (2011) Neutral and cationic chiral NCN pincer nickel(II) complexes with 1,3-bis(2'-imidazolinyl) benzenes: synthesis and characterization. Dalton Trans 40:9012-9013
76. Morales-Morales D, Grause C, Kasaoka K, Redo'n R, Cramer RE, Jensen CM (2000) Inorg Chim Acta 300-302:958-963
77. Bedford RB, Draper SM, Scully PN, Welch SL (2000) New J Chem 24:745-747
78. Gómez-Benítez V, Baldovino-Pantaleón O, Herrera-Á lvarez C, Toscano RA, Morales-Morales D (2006) Tetrahedron Lett 47:5059-5062
79. Pandarus V, Zargarian D (2007) Chem Commun 978-980
80. Pandarus V, Zargarian D (2007) Organometallics 26:4321-4334
81. Spasyuk D M, Sakhi HG, Zargarian D, unpublished results
82. Salah A, Zargarian D (2011) Dalton Trans 40:8977-8985
83. Chakraborty S, Krause JA, Guan H (2009) Organometallics 28:582-586
84. Zhang J, Medley CM, Krause JA, Guan H (2010) Organometallics 29:6393-6401
85. Chakraborty S, Patel YJ, Krause JA, Guan H (2011) Polyhedron doi:10.1016/j. poly.2011.04.030
86. Lefèvre X, Spasyuk DM, Zargarian D (2011) J Organomet Chem 696:864-870
87. Salah A, Offenstein C, Zargarian D (2011) Organometallics 30:5352-5364
88. Chakraborty S, Zhang J, Krause JA, Guan H (2010) J Am Chem Soc 132:8872-8873
89. Spasyuk DM, Salhi N-L, Zargarian D (unpublished results)
90. Tsou TT, Kochi JK (1979) J Am Chem Soc 101:7547-7560
91. Lefèvre X, Durieux G, Lesturgez S, Zargarian D (2011) J Mol Catal A Chem 335:1-7
92. Xu G, Li X, Sun H (2011) J Organomet Chem 696:3011-3014
93. Huang F, Zhang C, Jiang J, Wang Z-X, Guan H (2011) Inorg Chem 50:3816-3825
94. Al-Salem NA, Empsall HD, Markham R, Shaw BL, Weeks B (1979) J Chem Soc Dalton Trans 1972-1982
95. Al-Salem NA, McDonald WS, Markham R, Norton MC, Shaw BL (1980) J Chem Soc Dalton Trans 59-63
96. Crocker C, Errington JR, Markham R, Moulton CJ, Odel KJ, Shaw BL (1980) J Am Chem Soc 102:4373-4379
97. Gwynne EA, Stephan DW (2011) Nickel(II) and palladium(II) bis-aminophosphine pincer complexes. Organometallics 30:4128-4135
98. Spasyuk DM, Zargarian D, van der Est A (2009) Organometallics 28:6531-6540
99. Spasyuk DM, Zargarian D (2010) Inorg Chem 49:6203-6213
100. Spasyuk DM, Gorelsky SI, van der Est A, Zargarian D (2011) Inorg Chem 50:2661-2674
101. Zhang B-S, Wang W, Shao D-D, Hao X-Q, Gong J-F, Song M-P (2010) Organometallics 29:2579-2587
102. Yang M-J, Liu Y-J, Gong J-F, Song M-P (2011) Organometallics 30:3793-3803
103. Niu J-L, Chen Q-T, Hao X-Q, Zhao Q-X, Gong J-F, Song M-P (2010) Organometallics 29:2148-2156
104. Kruithof CA, Dijkstra HP, Lutz M, Spek AL, Gebbink RJMK, van Koten G (2008) Organometallics 27:4928-4937
105. Liu A, Zhang X, Chen W (2009) Organometallics 28:4868-4871
106. Ebeling G, Meneghetti MR, Rominger F, Dupont J (2002) Organometallics 21:3221-3227
107. Consorti CS, Ebeling G, Flores FR, Rominger F, Dupont J (2004) Adv Synth Catal 346:617-624
108. Chianese AR, Mo A, Lampland NL, Swartz RL, Bremer PT (2010) Organometallics 29:3019-3026