N-benzyl-N-phosphino-tert-butylsulfinamide and its coordination modes with Ir(I), Cu(I), Pd(II), and Pt(II): P,S or P,O?

Organometallics

Volumn 30, Issue 11, 2011, Pages 3119-3130

  Achard, Thierry ^a   Benet Buchholz, Jordi ^b   Escudero Adán, Eduardo C ^b   Riera, Antoni ^a   Verdaguer, Xavier ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION MODES; MONODENTATE P-LIGANDS; SOFT METALS;

IRIDIUM; LIGANDS; PALLADIUM; PALLADIUM COMPOUNDS;

PLATINUM;

EID: 79958142089     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200217j     Document Type: Article

References (112)

1. Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27.
2. Slone, C. S.; Weinberger, D. A.; Mirkin, C. A. The Transition Metal Coordination Chemistry of Hemilabile Ligands. In Progres in Inorganic Chemistry; Karlin, K. D., Ed.; Wiley: New York, 1999; Vol. 48, p 233.
3. Braunstein, P.; Naud, F. Angew. Chem., Int. Ed. 2001, 40, 680.
4. Bassetti, M. Eur. J. Inorg. Chem. 2006, 4473.
5. For CdC groups, see: Barthel-Rosa, L. P.; Maitra, K.; Nelson, J. H. Inorg. Chem. 1998, 37, 633.
6. Braunstein, P.; Naud, F.; Dedieu, A.; Rohmer, M.-M.; DeCian, A.; Rettig, S. J. Organometallics 2001, 20, 2966.
7. Muller, C.; Lachicotte, R. J.; Jones, W. D Organometallics 2002, 21, 1118.
8. Bassetti, M.; Alvarez, P.; Gimeno, J.; Lastra, E. Organometallics 2004, 23, 5127.
9. Faller, J. W.; Fontaine, P. P. J. Organomet. Chem. 2007, 692, 976.
10. For recent applications of sulfoxides in metal catalysis, see:Dorta, R.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2002, 124, 188.
11. Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346.
12. Mariz, R.; Luan, X.; Gatti, M.; Linden, A.; Dorta, R. J. Am. Chem. Soc. 2008, 130, 2172.
13. Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
14. Bürgi, J. J.; Mariz, R.; Gatti, M.; Drinkel, E.; Luan, X.; Blumentritt, S.; Linden, A.; Dorta, R. Angew. Chem., Int. Ed. 2009, 48, 2768.
15. Verdaguer, X.; Moyano, A.; Pericás, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. J. Am. Chem. Soc. 2000, 122, 10242.
16. Verdaguer, X.; Pericás, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868.
17. Verdaguer, X.; Lledó, A.; López-Mosquera, C.; Maestro, M. A.; Pericás, M. A.; Riera, A. J. Org. Chem. 2004, 69, 8053.
18. Solá, J.; Riera, A.; Verdaguer, X.; Maestro, M. A. J. Am. Chem. Soc. 2005, 127, 13629.
19. Ferrer, C.; Riera, A.; Verdaguer, X. Organometallics 2009, 28, 4571.
20. Ji, Y. N.; Riera, A.; Verdaguer, X. Org. Lett. 2009, 11, 4346.
21. Reves, M.; Riera, A.; Verdaguer, X. Eur. J. Inorg. Chem. 2009, 29-30, 4446.
22. Solá, J.; Revés, M.; Riera, A.; Verdaguer, X. Angew. Chem., Int. Ed. 2007, 46, 5020.
23. Revés, M.; Achard, T.; Sola, J.; Riera, A.; Verdaguer, X. J. Org. Chem. 2008, 73 (18), 7080.
24. Achard, T.; Benet-Buchholz, J.; Riera, A.; Verdaguer, X. Organometallics 2009, 28, 480.
25. Brun, S.; Parera, M; Pla-Quintana, A.; Roglans, A.; León, T.; Achard, T.; Solá, J.; Verdaguer, X.; Riera, A. Tetrahedron 2010, 66, 9032.
26. Wenschuh, E.; Fritzsche, B. J. Prakt. Chem. 1970, 312, 129.
27. Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715.
28. For general reviews on chiral sulfoxides see: Fernández, I.; Khiar, N. Chem. Rev. 2003, 103, 3651.
29. Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133.
30. Alcock, N. W.; Brown, J. M.; Evans, P. L. J. Organomet. Chem. 1988, 356, 233.
31. Ferrer, C.; Riera, A.; Verdaguer, X. Organometallics 2009, 28, 4571.
32. For DMSO as monodentate ligand see: Dorta, R.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. Chem.-Eur. J. 2003, 9, 5237.
33. For bidentate ligand see: Evans, D. R.; Huang, M.; Seganish, W. M.; Fettinger, J. C.; Williams, T. L. Inorg. Chem. Commun. 2003, 6, 462.
34. Cartwright, P. S. C.; Gillard, R. D.; Sillanpaa, E. R. J.; Valkonen, J. Tetrahedron 1988, 7, 2143.
35. Generally, O-bonding in sulfoxides results in small downfield chemical shifts of the R-protons (<0.5 ppm), while larger downfield chemical shifts (1 ppm) are seen for coordination through the S-atom. This trend is observed for the β- and γ-protons, although the extent of these effects decreases as the protons become further removed from the S-atom; see refs 14a and 15d and reference therein.
36. 3) of the free ligand (R)-1a for both t-Bu and methylene proton are 0.93, 4.46, and 4.60, respectively.
37. Selected reviews: Kagan, H. B.; Ronnan, B. Rev. Heteroat. Chem. 1992, 7, 92. For review on DMSO bound to metal see:
38. Calligaris, M.; Carugo, O. Coord. Chem. Rev. 1996, 153, 83.
39. Calligaris, M. Coord. Chem. Rev. 2004, 248, 351.
40. Alessio, E. Chem. Rev. 2004, 104, 4203.
41. Li, J. R.; Bu, X. H. Eur. J. Inorg. Chem. 2008, 27.
42. Kitching, W.; Moore, C. J.; Doddrell, D. Aust. J. Chem. 1969, 22, 1149.
43. Kitching, W.; Moore, C. J.; Doddrell, D. Inorg. Chem. 1970, 9, 541.
44. Jaswal, J. S.; Yapp, D. T. T.; Rettig, S. J.; James, B. R.; Skov, K. A. J. Chem. Soc., Chem. Commun. 1992, 1528.
45. Pettinari, C.; Pellei, M.; Cavicchio, G.; Crucianelli, M.; Panzei, W.; Colapietro, M.; Cassetta, A. Organometallics 1999, 18, 555.
46. Iridium 2a and 2b complexes displayed vS-O bands at 1031 and 1056 cm-1, respectively, more shielded than the corresponding free ligand at 1074 cm-1, which go to the opposite trend observed for other sulfoxide groups; see refs 9a, 11b, and 12.
47. For S- and O-bonded sulfone see: Sykes, A.; Mann, K. R. J. Am. Chem. Soc. 1988, 110, 8252.
48. Randall, S. L.; Miller, C. A.; Janik, T. S.; Churchill, M. R.; Atwood, J. D. Organometallics 1994, 13, 141.
49. Calligaris reported only seven X-ray images of iridium complexes, one Ir(I) and six Ir(III), and all of them are S-bonded to the metal; see ref 11b. Recently Milstein reported more X-ray structures of S-bonded complexes and the high difficulty to isolate such an O-Ir(I) complex with DMSO; see ref 14a. For an S-bonded heterobimetallic complex see: Sykes, A.; Mann, K. R. J. Am. Chem. Soc. 1988, 110, 8252.
50. Delta;δ calculated from the free ligand 1a at 60 ppm.
51. 31P NMR values for complexes III-(cod), 116.5 ppm, and for bis-PNSO IV, 69.5 ppm; see ref 6.
52. For Rh(I) complexes see: Wiester, J. M.; Braunscheig, A:B; Mirkin, C. A. Inorg. Chem. 2010, 49, 7188.
53. For solvent effects in a supramolecular system see:(b) Leigh, D. A.; Morales, M. A. F.; Perez, E. M.; Wong, J. K. Y.; Saiz, C. G.; Slawin, A. M. Z.; Carmichael, A. J.; Haddleton, D. M.; Brouwer, A. M.; Buma, W. J.; Wurpel, G. W. H.; Leon, S.; Zerbetto, F. Angew. Chem., Int. Ed. 2005, 44, 3062.
54. Precedent for this type of structural arrangement exists for Ir P, S ligands: Malacea, R.; Manoury, E.; Routaboul, L.; Daran, J. C.; Poli, R.; Dunne, J. P.; Withwood, A. C.; Godard, C.; Duckett, S. B. Eur. J. Inorg. Chem. 2006, 9, 1803. and P,N ligands:
55. Lo Schiavo, S.; Grassi, M.; De Munno, G.; Nicolo, F.; Tresoldi, G. Inorg. Chim. Acta 1994, 216, 209.
56. Tejel, C.; Bravi, R.; Ciriano, M. A.; Oro, L. A.; Bordonaba, M.; Graiff, C.; Tiripicchio, A.; Burini, A. Organometallics 2000, 19, 3115.
57. Owens, T. D.; Hollander, F. J.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539.
58. Tsujimoto, T.; Ishihara, J.; Horie, M.; Murai, A. Synlett 2002, 399.
59. Owens, T. D.; Souers, A. J.; Ellman, J. A. J. Org. Chem. 2003, 68, 3.
60. Emokpae, T. A.; Ukwueze, A. C.; Walton, D. R.; Hitchockok, P. B. Synth. R. Inorg. Met-Org. Chem. 1986, 16, 387.
61. Geremia, S.; Calligaris, M.; Mestroni, S. Inorg. Chim. Acta 1999, 292, 144.
62. Francisco, R. H. P.; Gambardella, M. T. P.; Rodrigues, A. M. G. D.; De Souza, G. F.; Filgueiras, C. A. L. Acta Crystallogr., Sect. C 1995, 51, 604.
63. Filgueiras, C. A. L.; Holland, P. R.; Johnson, B. F. G.; Raithby, P. R. Acta Crystallogr., Sect. B 1982, 38, 2684.
64. Zhu, F. C.; Shao, P. X.; Yao, X. K.; Wang, R. J.; Wang, H. G. Inorg. Chim. Acta 1990, 171, 85.
65. Carvalho, C. C.; Francisco, R. H. P.; Gambardella, M. T. P.; De Souza, G. F.; Filgueiras, C. A. L. Acta Crystallogr., Sect. C 1996, 52, 1627.
66. Acta Crystallogr., Sect. C 1996, 52, 1629.
67. Saravanabharatani, D.; Nethaji, M.; Samuelson, A. G. Polyhedron 2002, 21, 2793.
68. Côté, A.; Charette, A. B. J. Org. Chem. 2005, 70, 10864.
69. Grinberg, A. A.; Gel'fma, M. I.; Kiseleva, N. V. Russ. J. Inorg. Chem. (Engl Transl.) 1967, 12, 620.
70. Schramm, R. F.; Wayland, B. B. Chem. Commum. 1968, 898.
71. Price, J. H.; Williamson, A. N.; Schramm, R. F.; Wayland, B. B. Inorg. Chem. 1972, 11, 1280.
72. Bolm, C.; Kaufmann, D.; Zehnder, M.; Neuburger, M. Tetrahedron Lett. 1996, 37, 3985.
73. Bolm, C.; Simiae, O.; Martin, M. Synlett 2001, 1878.
74. Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
75. Reetz, M. T.; Bondarev, O. G.; Gais, H.-J.; Bolm, C. Tetrahedron Lett. 2005, 46, 5643.
76. Lai, H.; Huang, Z.; Wu, Q.; Qin, Y. J. Org. Chem. 2009, 74, 283.
77. These isomers are often designated as exo and endo when there is an obvious reference point out of the plane of the square-planar metal moiety; see: Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2108.
78. This description, however, is ambiguous for a planar PdXY set or in cases where a reference point is not clear. One might view this as a case of planar chirality; however, a nomenclature based on axial chirality was suggested by Hayashi: Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681.
79. This can be awkward when dealing with "axial chirality" of both the ligand and the metal. Faller et al. consider the Pd system as one would a chiral pyramidal phosphorus atom, considering the allyl as an 18-electron pseudoatom placed at the centroid of the allyl: Faller, J. W.; Sarantopoulos, N. Organometallics 2004, 23, 2008.
80. Albert, J.; Bosque, R.; Cadena, J. M.; Delgado, S.; Granell, J.; Muller, G.; Ordinas, J. I.; Font Bardia, M.; Solans, X. Chem.-Eur. J. 2002, 8, 2279.
81. Boele, M. D. K.; Kamer, P. C. J.; Lutz, M.; Spek, A. L.; de Vries, J. G.; van Leeuwen, P. W. N. M.; van Strijdonck, G. P. F. Chem.-Eur. J. 2004, 10, 6232.
82. Mason, R.; Russell, D. R. Chem. Commun. 1996, 26.
83. Filipuzzi, S.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2006, 25, 5955.
84. Powell, J.; Shaw, B. L. J. Chem. Soc. 1967, 1839.
85. For a nice review see: Nishio, M. CrystEngComm 2004, 6, 130.
86. Kodama, Y.; Nishihata, K.; Nishio, M.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 2 1976, 1490.
87. Onaka, S.; Furuta, H.; Takagi, S. Angew. Chem., Int. Ed. Engl. 1993, 32, 87.
88. Jitsukawa, K.; Iwai, K.; Masuda, H.; Ogoshi, H.; Einaga, H. Chem. Lett. 1994, 303.
89. Suezawa, H.; Yoshida, T.; Umezawa, Y.; Tsuboyama, S.; Nishio, M. Eur. J. Inorg. Chem. 2002, 3148.
90. Braga, D.; Grepioni, F.; Tedesco, E. C. Organometallics 1998, 17, 2669.
91. Review: Okawa, H. Coord. Chem. Rev. 1988, 92, 1.
92. Sakiyama, H.; Okawa, H.; Matsumoto, N.; Kida, S. J. Chem. Soc., Dalton Trans. 1990, 2935.
93. Colquhoun, H. M.; Doughty, S. M.; Stoddart, J. F.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1986, 1639.
94. Colquhoun, H. M.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1986, 25, 487.
95. This short distance is significantly smaller than the relevant Van Der Waals radii: Suezawa, H.; Yoshida, T.; Umezawa, Y.; Tsuboyama, S.; Nishio, M. Eur. J. Inorg. Chem. 2002, 3148.
96. Scrivanti et al. reported an X-ray structure of cationic palladium complexes that revealed a CH/p interaction between the anti- allyl proton and a phenyl-phosphine group; see: Scrivanti, A.; Benetollob, F.; Venzoc, A.; Bertoldinia, M.; Beghettoa, V.; Matteolia, U. J. Organomet. Chem. 2007, 692, 3577.
97. Nishio, M.; Umezawa, Y.; Kazumasa, H.; Tsuboyama, S.; Suezawa, H. CrystEngComm 2009, 11, 1757.
98. Different palladium sources were tested and always gave the same results in THF.
99. For Pt(II) see: Elding, L. I.; Oskarsson, A. Inorg. Chem. Acta. 1987, 130, 209.
100. For Pt(III) see:(b) Cotton, F. A.; Falvello, L. R.; Han, S. Inorg. Chem. 1982, 21, 2889.
101. For a review on bis-sulfoxides, see: Delouvrié, B.; Fensterbank, L.; Nájera, F.; Malacria, M. Eur. J. Org. Chem. 2002, 3507.
102. Madan, K.; Hull, C. M.; Herman, L. J. Inorg. Chem. 1968, 7, 491.
103. Cattalini, L.; Michelon, G.; Marangoni, G.; Pelizzi, G. J. Chem. Soc., Dalton Trans. 1979, 96.
104. Filgueiras, C. A. L.; Holand, P. R.; Johnson, B. F. G.; Raithby, P. R. Acta Crystallogr. B 1982, B38, 954.
105. Guo, N.; Lin, Y.-H.; Xi, S.-Q. Acta Crystallogr. C 1995, C51, 619.
106. Evans, D. R.; Huang, M.; Seganish, W. M.; Fettinger, J. C.; Williams, T. L. Inorg. Chem. Commun. 2003, 6, 462.
107. Mallorquin, R. M.; Chelli, S.; Brebion, F.; Fensterbank, L.; Goddard, J. P.; Malacria, M. Tetrahedron: Asymmetry 2010, 21, 1695.
108. The distance between the two centroids was measured by using Mercury software.
109. Steed, J.W.; Atwood, J. L. Supramolecular Chemistry; Wiley: Chichester, 2000.
110. For a review see: Roesky, H. W.; Andruh, M. Coord. Chem. Rev. 2003, 236, 91.
111. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1-S83.
112. Rochon, F. D.; Kong, P. C.; Melanson, R. Inorg. Chem. 1990, 29, 1352.