Non-innocent Behaviour of Dithiocarboxylate Ligands Based on N-Heterocyclic Carbenes

[en] The ruthenium(II) complex [Ru(CH=CHC6H4Me-4)(κ2-S2C•NHC)(CO)(PPh3)2]+ is formed on reaction of NHC•CS2 (NHC = ICy, IMes) with [Ru(CH=CHC6H4Me-4)Cl(CO)(BTD)(PPh3)2] in the presence of NH4PF6, whereas the analogous reaction with the more bulky IDip•CS2 leads to the remarkable product, [Ru{κ2-SC(H)S(CH=CHC6H4Me-4)•IDip}Cl(CO)(PPh3)2]+.

Disciplines :

Chemistry

Author, co-author :

Naeem, Saira

Thompson, Amber L.

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Wilton-Ely, James D. E. T.

Language :

English

Title :

Non-innocent Behaviour of Dithiocarboxylate Ligands Based on N-Heterocyclic Carbenes

Publication date :

2010

Journal title :

Chemistry

ISSN :

0947-6539

eISSN :

1521-3765

Publisher :

Wiley, Weinheim, Germany

Volume :

Issue :

Pages :

10971-10974

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 16 November 2010

Statistics

Number of views

88 (3 by ULiège)

Number of downloads

0 (0 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

Bibliography

For reviews on the coordination chemistry of dithio ligands, see: a) D. Coucouvanis. Prog. Inorg. Chem. 1970. 11, 233-371;
b) D. Coucouvanis, Prog. Inorg. Chem. 1979, 26, 301-469;
c) R. P. Burns, F. P. McCullough, C. A. McAuliffe, Adv. Inorg. Chem. Radiochem. 1980, 22, 211-280;
d) G. Hogarth. Prog, Inorg. Chem. 2005, 53, 71 -561;
e) E. R.T. Tiekink, I. Haiduc, Prog. Inorg. Chem. 2005, 54, 127-319.
For reviews of NHCs, see: a) W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282;
Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187;
b) W. A. Herrmann. Angew. Chem. 2002, 114, 1342-1363;
Angew. Chem. Int. Ed. 2002, 41, 1290-1309;
c) F. E. Hahn, M.C. Jahnke, Angew. Chem. 2008, 120, 3166-3216;
Angew. Chem. Int. Ed. 2008, 47, 3122-3172.
For recent examples, see: a) S. P. Nolan, Eur, J. Inorg. Chem. 2009, 1664, and following papers in this issue;
b) F. E. Hahn. Dalton Trans. 2009, 6893, and following papers in this issue;
c) A. J. Arduengo III, G. Bertrand, Chem. Rev. 2009, 109, 3209-3210, and following papers in this issue.
For selected reviews, see: a) L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2000, 46, 181-222;
b) W. A. Herrmann. T. Weskamp, V. P. W. Böhm. Adv. Organomet. Chem. 2001, 48, 1-69;
c) C. M. Crudden. D. P. Allen, Coord. Chem. Rev. 2004, 248, 2247-2273;
d) N. M. Scott, S. P. Nolan, Eur. J. Inorg. Chem. 2005, 1815-1828;
e) J. C. Garrison, W. J. Youngs, Chem. Rev. 2005, 105, 3978-4008;
f) V. Dragutan, I. Dragutan. L. Delaude, A. Demonceau, Coord. Chem. Rev. 2007, 251, 765-794;
g) W. J. Sommer, M. Weck, Coord. Chem. Rev. 2007, 251, 860-873;
h)N. Marion, S. P. Nolan, Chem. Soc. Rev. 2008, 37, 1776-1782.
a) A. Igau. H. Grutzmacher, A. Baceiredo, G. Bertrand. J. Am. Chem. Soc. 1988, 110, 6463-6466;
b) A. Igau, A. Baceiredo, G. Trinquier, G. Bertrand, Angew. Chem. 1989, 101, 617-618;
Angew. Chem. Int. Ed. Engl. 1989, 28, 621-622;
c) A.J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361-363;
d)A.J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 2801;
e) A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913-921;
f) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-92.
a)H.-W. Wanzlick, H.-J. Kleiner, Angew. Chem. 1961, 73, 493;
b) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134;
c) D. M. Lemal, K. I. Kawano, J. Am. Chem. Soc. 1962, 84, 1761-1762;
d) H.-W. Wanzlick, F. Esser, H.-J. Kleiner, Chem. Ber. 1963, 96, 1208-1212;
e) D. M. Lemal. R. A. Lovald, K. I. Kawano, J. Am. Chem. Soc. 1964, 86, 2518-2519:
f) H.-W. Wanzlick, B. Lachmann, E. Schikora, Chem. Ber. 1965, 98, 3170-3177;
g) H. E. Winberg, J. E. Carnahan, D. D. Coffman, M. Brown, J. Am. Chem. Soc. 1965, 87, 2055-2056.
For a review, see: L. Delaude, Eur. J. Inorg. Chem. 2009, 1681-1699.
a) N. Kuhn, T. Kratz, Synthesis 1993, 561-562:
b) N. Kuhn. H. Bohnen, G. Henkel. Z. Naturforsch. B 1994, 49, 1473-1480;
c) D. Enders. K. Breuer, J. Runsink, J. H. Teles, Liebigs Ann. Chem. 1996, 2019-2028;
d) N. Kuhn, E. Niquet. M. Steimann, I. Walker, Z. Naturforsch. B 1999, 54, 1181-1187;
e) R. Faust. B. Göbelt, Chem. Commun. 2000, 919-920;
f) L. Delaude, A. Demonceau, J. Wouters, Eur. J. Inorg. Chem. 2009, 1882-1891.
a) L. L. Borer, J. V. Kong, Inorg. Chim. Acta 1986, 122, 145-148;
b) L. L. Borer. J. V. Kong, P. A. Keihl, D. M. Forkey. Inorg. Chim. Acta 1987, 129, 223-226.
O. Kaufhold, F. E. Hahn, Angew. Chem. 2008, 120, 4122-4126;
Angew. Chem. Int. Ed. 2008, 47, 4057-4061
a) M. J. Macgregor. G. Hogarth, A. L. Thompson, J. D. E. T. WiltonEly, Organometallics 2009, 28, 197-208;
b) E. R. Knight, A. R. Cowley. G. Hogarth, J. D. E. T. Wilton-Ely, Dalton Trans. 2009, 607-609;
c) E. R. Knight, N. H. Leung, Y. H. Lin. A. R. Cowley, D. J. Watkin, A. L. Thompson, G. Hogarth. J. D. E. T. Wilton-Ely, Dalton Trans. 2009, 3688-3697;
d) E. R. Knight. N. H. Leung, A. L. Thompson, G. Hogarth, J. D. E. T. Wilton-Ely, Inorg. Chem. 2009, 48, 3866-3874;
e) J. D. E. T. Wilton-Ely, D. Solanki. E. R. Knight, K. B. Holt, A. L. Thompson. G. Hogarth, Inorg. Chem. 2008, 47, 9642-9653.
a) L. Delaude, X. Sauvage, A. Demonceau, J. Wouters, Organometallics 2009, 28, 4056-4064;
b) S. Naeem, L. Delaude, A. J. P. White, J. D. E. T. Wilton-Ely, Inorg. Chem. 2010, 49, 1784-1793.
M. R. Torres, A. Vegas, A. Santos, J. Ros, J. Organomet. Chem. 1986, 309, 169-177.
M. C. J. Harris, A. F. Hill, Organometallics 1991, 10, 3903-3906.
a) H. Loumrhari, J. Ros. M. R. Torres, Polyhedron 1991, 10, 421-427;
b) R. B. Bedford, C. S. J. Cazin, J. Organomet. Chem. 2000, 598, 20-23;
c) J. D. E. T. Wilton-Ely, D. Solanki. G. Hogarth, Eur. J. Inorg. Chem. 2005, 4027-4030.
Y. H. Lin, N. H. Leung, K. B. Holt, A. L. Thompson, J. D. E. T. Wilton-Ely, Dalton Trans. 2009, 7891-7901.
A. L. Hector, A. F. Hill, J. Organomet. Chem. 1993, 447, C7-C9.
Single crystal diffraction data were collected at low temperature [22] by using an Enraf-Nonius KCCD diffractometer.[23] The crystal structures of 2 and 6 were solved by using SIR92[24] and refined by using the CRYSTALS software suite,[25] as per the Supporting Information (CIF file). The data for 6 were shown to be twinned and were dealt with using ROTAX.[26] CCDC-767136 (2) and 767137 (6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif.
A. R. Cowley, A. L. Hector, A. F. Hill, A. J. P. While, D. J. Williams, J. D. E. T. Wilton-Ely, Organometallics 2007, 26, 6114-6125.
a) D. J. Cook, K. J. Harlow, A. F. Hill, T. Welton, A. J. P. White, D. J. Williams, New J. Chem. 1998, 22, 311-313;
b) K. J. Harlow, A. F. Hill, T. Welton, A. J. P. White, D. J. Williams, Organometallics 1998, 17, 1916-1918.
a) J. D. E. T. Wilton-Ely, P. J. Pogorzelec, S. J. Honarkhah, D. A. Tocher, Organometallics 2005, 24, 2862-2874;
b) J. D. E. T. WiltonEly, S. J. Honarkhah, M. Wang, D. A. Tocher. Dalton Trans. 2005, 1930-1939;
c)J. D.E.T. Wilton-Ely, M. Wang, D. Benoit. D. A. Tocher, Eur. J. Inorg. Chem. 2006, 3068-3078.
J. Cosier, A. M. Glazer, J. Appl. Crystallogr. 1986, 19, 105-107.
Z. Otwinowski, W. Minor Macromolecular Crystallography Part A in Methods in Enzymotogy, Vol.276 (Eds.: C.W. Carter, Jr. R. M. Sweet), Academic Press, New York, 1997, pp. 307-326.
A. Altomare. G. Cascarano. C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435-435.
P. W. Betteridge, J. R. Carruthers, R. I. Cooper. K. Prout, D. J. Watkin, J. Appl. Crystallogr. 2003, 56, 1487-1487.
R. I. Cooper, R. O. Gould, S. Parsons. D. J. Watkin, J. Appl. Crystatlogr. 2002, 35, 168-174.