Organometallics
Article
see: (e) Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. J. Med.
Chem. 1986, 29, 2262−2267. (f) Alvarez, R.; Velazquez, S.; San-Felix,
A.; Aquaro, S.; De Clercq, E.; Perno, C. F.; Karlsson, A.; Balzarini, J.;
Camarasa, M. J. J. Med. Chem. 1994, 37, 4185−4194. (g) Chen, M. D.;
Lu, S. J.; Yuag, G. P.; Yang, S. Y.; Du, X. L. Heterocycl. Commun. 2000,
6, 421−426. (h) Genin, M. J.; Allwine, D. A.; Anderson, D. J.;
Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega,
K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford,
C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi,
B. H. J. Med. Chem. 2000, 43, 953−970.
(15) (a) Jafarpour, L.; Stevens, E. D.; Nolan, S. P. J. Organomet.
Chem. 2000, 606, 49−54. (b) Huang, J.; Stevens, E. D.; Nolan, S. P.;
Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674−2678.
(16) Johnson, T. J.; Folting, K.; Strieb, W. E.; Martin, J. D.; Huffman,
J. C.; Jackson, S. A.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 1995,
34, 488−499.
(17) Tam, A.; Arnold, U.; Soellner, M. B.; Raines, R. T. J. Am. Chem.
Soc. 2007, 129, 12670−12671.
1
(18) Complete H spectra and accompanying 31P NMR spectra are
given in Supporting Information Figures S1 and S2.
(19) See Supporting Information for NMR spectra characterization
of η2-HCCPh Ru complex 10.
(2) (a) Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565−598.
(b) Huisgen, R. 1,3-Dipolar Cycloadditional Chemistry; Padwa, A., Ed.;
Wiley: New York, 1984.
1
(20) Complete H spectra and accompanying 31P NMR spectra are
given in Supporting Information Figures S3 and S4.
(3) Wang, Q.; Chittaboina, S.; Barnhill, H. N. Lett. Org. Chem. 2005,
(21) Kirchner, K.; Calhorda, M. J.; Schmid, R.; Veiros, L. F. J. Am.
Chem. Soc. 2003, 125, 11721−11729 , and reference therein.
(22) (a) Albers, M. O.; de Waal, D. J. A.; Liles, D. C.; Robinson, D.
J.; Singleton, E.; Wiege, M. B. J. Chem. Soc., Chem. Commun. 1986,
1680−1682. (b) Campion, B. K.; Heyn, R. H.; Don Tilley, T.
Organometallics 1990, 9, 1106−1112.
2, 293−301.
(4) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002,
67, 3057−3064.
(5) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B.
Angew. Chem., Int. Ed. 2002, 41, 2596−2599.
(6) (a) Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.;
Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127,
15998−15999. (b) Rasmussen, L. K.; Boren, B. C.; Fokin, V. V. Org.
Lett. 2007, 9, 5337−5339. (c) Boren, B. C.; Narayan, S.; Rasmussen, L.
K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc.
2008, 130, 8923−8930.
(23) Zhang, L.; Sung, H. H.-Y.; Williams, I. D.; Lin, Z.; Jia, G.
Organometallics 2008, 27, 5122−5129.
(24) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635−646.
(25) (a) Cenini, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.;
Piangiolino, C. Coord. Chem. Rev. 2006, 250, 1234−1253.
(b) Bebbington, M. W. P.; Bourissou, D. Coord. Chem. Rev. 2009,
253, 1248−1261. (c) Hillhouse, G. L.; Goeden, G. V.; Haymore, B. L.
Inorg. Chem. 1982, 21, 2064−2071. (d) Fortman, G. C.; Captain, B.;
Hoff, C. D. Organometallics 2009, 28, 3587−3590. (e) Liu, B.; Cui, D.
Dalton Trans. 2009, 550−556.
(7) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed.
2001, 40, 2004−2021.
(8) (a) Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952−
3015. (b) Feldman, A. K.; Colasson, B.; Sharpless, K. B.; Fokin, V. V. J.
Am. Chem. Soc. 2005, 127, 13444−13445. (c) Rodionov, V. O.;
Presolski, S. I.; Díaz, D.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc.
2007, 129, 12705−12712. (d) Dutta, B.; Curchod, B. F. E.;
Campomanes, P.; Solari, E.; Scopelliti, R.; Rothlisberger, U.; Severin,
K. Chem.Eur. J. 2010, 16, 8400−8409.
(26) Danopoulos, A. A.; Hay-Motherwell, R. S.; Wilkinson, G.;
Cafferkey, S. M.; Sweet T. K. N. Hursthouse, M. B. J. Chem. Soc.,
Dalton Trans. 1997, 3177−3184.
(27) Michelman, R. I.; Bergman, R. G.; Andersen, R. A.
Organometallics 1993, 12, 2741−2751.
(28) CCDC 820903 (17) contains the supplementary crystallo-
graphic data for this contribution. These data can be obtained free of
charge from The Cambridge Crystallographic Data Centre via www.
(29) Frisch, M. J.;et al. Gaussian03; Gaussian, Inc.: Pittsburgh, PA,
2003.
(30) (a) Becke, A. Phys. Rev. A 1988, 38, 3098−3100. (b) Perdew, J.
P. Phys. Rev. B 1986, 33, 8822−8824. (c) Perdew, J. P. Phys. Rev. B
1986, 34, 7406−7406.
(31) Schaefer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97,
2571−2577.
(32) Kuechle, W.; Dolg, M.; Stoll, H.; Preuss, H. J. Chem. Phys. 1994,
100, 7535−7542.
(33) (a) Poater, A.; Ragone, F.; Correa, A.; Cavallo, L. J. Am. Chem.
Soc. 2009, 131, 9000−9006. (b) Poater, A.; Cavallo, L. J. Mol. Catal. A
2010, 324, 75−79. (c) Bosson, J.; Poater, A.; Cavallo, L.; Nolan, S. P. J.
Am. Chem. Soc. 2010, 132, 13146−13149. (d) Nun, P.; Gaillard, S.;
Poater, A.; Cavallo, L.; Nolan, S. P. Org. Biomol. Chem. 2011, 9, 101−
104. (e) Poater, A.; Ragone, F.; Correa, A.; Szadkowska, A.;
Barbasiewicz, M.; Grela, K.; Cavallo, L. Chem.Eur. J. 2011, 16,
14354−14364. (f) Mariz, R.; Poater, A.; Gatti, M.; Drinkel, E.; Burgi, J.
J.; Luan, X. J.; Blumentritt, S.; Linden, A.; Cavallo, L.; Dorta, R.
Chem.Eur. J. 2010, 16, 14335−14347. (g) Poater, A.; Ragone, F.;
Mariz, R.; Dorta, R.; Cavallo, L. Chem.Eur. J. 2010, 16, 14348−
14353.
(9) (a) Majireck, M. M.; Weinreb, S. M. J. Org. Chem. 2006, 71,
8680−8683. (b) Hou, D.-R.; Kuan, T.-C.; Li, Y.-K.; Lee, R.; Huang,
K.-W. Tetrahedron 2010, 66, 9415−9420. (c) Zhang, C. T.; Zhang, X.;
Qing, F.-L. Tetrahedron Lett. 2008, 49, 3927−3930. (d) Oppilliart, S.;
Mousseau, G.; Zhang, L.; Jia, G.; Thuery, P.; Rousseau, B.; Cintrat, J.
C. Tetrahedron 2007, 63, 8094−8098. (e) Yamamoto, Y.; Kinpara, K.;
Nishiyama, H.; Itoh, K. Adv. Synth. Catal. 2005, 347, 1913−1916.
(10) NHC-copper complexeswere found highly efficient catalysts for
the CuAAC reaction. See,for example: Díez- Gonzal
Angew. Chem., Int. Ed. 2008, 47, 8881−8884.
́
ez, S.; Nolan, S. P.
(11) (a) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P.
Organometallics 1999, 18, 2370−2375. (b) Campion, B. K.; Heyn, R.
H.; Tilley, T. D. J. Chem. Soc., Chem. Commun. 1988, 278−280.
(c) Johnson, T. J.; Folting, K.; Streib, W. E.; Martin, J. D.; Huffman, J.
C.; Jackson, S. A.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 1995, 34,
488−499.
(12) (a) Luo, L.; Nolan, S. P. Organometallics 1994, 13, 4781−4786.
(b) Li, C.; Luo, L.; Nolan, S. P.; Marshall, W.; Fagan, P. J.
Organometallics 1996, 15, 3456−3462.
(13) (a) Poater, A.; Cosenza, B.; Correa, A.; Giudice, S.; Ragone, F.;
Scarano, V.; Cavallo, L. Eur. J. Inorg. Chem. 2009, 1759−1766.
(b) Jacobsen, H.; Correa, A.; Poater, A.; Costabile, C.; Cavallo, L.
Coord. Chem. Rev. 2009, 253, 687−703. (c) Poater, A.; Ragone, F.;
Giudice, S.; Costabile, C.; Dorta, R.; Nolan, S. P.; Cavallo, L.
Organometallics 2008, 27, 2679−2681. (d) Ragone, F.; Poater, A.;
Cavallo, L. J. Am. Chem. Soc. 2010, 132, 4249−4258. (e) Poater, A.;
Cavallo, L. Dalton Trans. 2009, 8878−8883. (f) Clavier, H.; Nolan, S.
P. Chem. Commun. 2010, 46, 841−861. (g) Luan, X.; Mariz, R.; Gatti,
M.; Costabile, C.; Poater, A.; Cavallo, L.; Linden, A.; Dorta, R. J. Am.
Chem. Soc. 2008, 130, 6848−6858. (h) Credendino, R.; Poater, A.;
Ragone, F.; Cavallo, L. Catal. Sci. Technol. 2011, 1, 1287−1297.
(14) Hiller, A. C.; Sommer, W. J.; Yong, B. S.; Petersen, J. L.; Cavallo,
L.; Nolan, S. P. Organometallics 2003, 22, 4322−4326.
(34) (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027−2094.
(b) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995−2001.
767
dx.doi.org/10.1021/om2012425 | Organometallics 2012, 31, 756−767