Contrasting Reactivity of 2-Mesityl-1,8-Naphthyridine (Mes-NP) with Singly-Bonded [RhII–RhII] and [RuI–RuI] Compounds
Biswajit Saha A , S. M. Wahidur Rahaman A , Arup Sinha A and Jitendra K. Bera A BA Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India.
B Corresponding author. Email: jbera@iitk.ac.in
Australian Journal of Chemistry 64(5) 583-589 https://doi.org/10.1071/CH11060
Submitted: 3 February 2011 Accepted: 12 April 2011 Published: 30 May 2011
Abstract
Reaction of cis-[Rh2(CH3COO)2(CH3CN)6](BF4)2 with two equivalents of 2-mesityl-1,8-naphthyridine (Mes-NP) affords trans-[Rh2(CH3COO)2(Mes-NP)2](BF4)2 (1). X-ray structure reveals weak Rh–C(ipso) interaction, and a short Rh–Rh distance. The same ligand, in contrast, oxidatively cleaves the Ru–Ru bond in cis-[Ru2(CO)4(CH3CN)6](BF4)2 and results in trans-[Ru(Mes-NP)2(CH3CN)2](BF4)2 (2). Both compounds adopt trans geometry to relieve the steric strain. Compound 2 exhibits moderate activity for the alcohol oxidation and aldehyde olefination reactions.
References
[1] J. K. Bera, N. Sadhukhan, M. Majumdar, Eur. J. Inorg. Chem. 2009, 4023 and references therein.| Crossref | GoogleScholarGoogle Scholar |
[2] M. Majumdar, A. Sinha, T. Ghatak, S. K. Patra, N. Sadhukhan, S. M. W. Rahaman, J. K. Bera, Chem. Eur. J. 2010, 16, 2574.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXitF2qur4%3D&md5=dc72cf586398f4b021e77c06eed9f61fCAS |
[3] R. K. Das, B. Saha, S. M. W. Rahaman, J. K. Bera, Chem. Eur. J. 2010, 16, 14459.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXit1Grug%3D%3D&md5=2bcddee9e1e8bc6258336955cd48ecd6CAS |
[4] A. Sinha, T. Ghatak, J. K. Bera, Dalton Trans. 2010, 39, 11301.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVOktr3F&md5=b47dc8dde0184f217af00283fb2a8682CAS | 20877891PubMed |
[5] S. K. Patra, S. M. W. Rahaman, M. Majumdar, A. Sinha, J. K. Bera, Chem. Commun. 2008, 2511.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmtlSis74%3D&md5=2f87eb7341e1a21cbad99ebad1aeec2dCAS |
[6] N. Sadhukhan, J. K. Bera, Inorg. Chem. 2009, 48, 978.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsFejurzK&md5=4a9c44fa5f2bcfc56c735ab74f6dabf6CAS | 19105751PubMed |
[7] S. K. Patra, J. K. Bera, Organometallics 2007, 26, 2598.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjs1SksL4%3D&md5=c3c462088ebbb2ff2600c556f38384f4CAS |
[8] S. K. Patra, N. Sadhukhan, J. K. Bera, Inorg. Chem. 2006, 45, 4007.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XjsFKiurk%3D&md5=cbee5e1857faaa1b63842cb5c7484d26CAS | 16676961PubMed |
[9] M. Majumdar, S. K. Patra, M. Kannan, K. R. Dunbar, J. K. Bera, Inorg. Chem. 2008, 47, 2212.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhslKnsbg%3D&md5=aa7746151c23e91596a42c11af6bfc7cCAS | 18269221PubMed |
[10] M. Majumdar, S. M. W. Rahaman, A. Sinha, J. K. Bera, Inorg. Chim. Acta 2010, 363, 3078.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1emtLjN&md5=40dcf5aad207c9caef76ead36aee8ee1CAS |
[11] S. K. Patra, J. K. Bera, Organometallics 2006, 25, 6054.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1WhsL7J&md5=8e084d118d73e896bd232d58a56b0da5CAS |
[12] S. K. Patra, M. Majumdar, J. K. Bera, J. Organomet. Chem. 2006, 691, 4779.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVygtb7F&md5=df6a20e5fccbe3373225f319bb871630CAS |
[13] M. A. Petrukhina, A. S. Filatov, Y. Sevryugina, K. W. Andreini, S. Takamizawa, Organometallics 2006, 25, 2135.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XivFemu7k%3D&md5=332c30eba875a59ab15c083b6fd9d6adCAS |
[14] M. A. Petrukhina, Y. Sevryugina, A. Yu. Rogachev, E. A. Jackson, L. T. Scott, Angew. Chem. Int. Ed. 2006, 45, 7208.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1Cltb7K&md5=3beac98b9f1d1193f8a433cab713c116CAS |
[15] M. A. Petrukhina, Angew. Chem. Int. Ed. 2008, 47, 1550.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXis1KrsL4%3D&md5=a39021409c4b0ee6afd1811a7051a474CAS |
[16] A shorter Rh–Rh distance of 2.356(1) Å is found in cis-[Rh2(μ-O2CCH3)2(η3-pynp)(η1-pynp)(NCCH3)2](BF4)(PF6)·2CH3CN compound. However the less yield of this compound regarded as minor product of the reaction. Campos-Fernández C. S.Thomson L. M.Galán-Mascarós J. R.Ouyang X.Dunbar K. R. Inorg. Chem. 2002, 41,
[17] I. B. Baranovskii, M. A. Golubnichaya, L. M. Dikareva, Russ. J. Inorg. Chem. 1982, 27, 1158.
[18] L. M. Dikareva, M. A. Golubnichaya, I. B. Baranovskii, Russ. J. Inorg. Chem. 1988, 33, 1179.
[19] F. P. Pruchnik, A. Jutarska, Z. Ciunik, M. Pruchnik, Inorg. Chim. Acta 2004, 357, 3019.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXlslKgsL0%3D&md5=089d0a9d59b31e4881b7d12e771927b1CAS |
[20] T. Yoshimura, K. Umakoshi, Y. Sakai, Chem. Lett. 1999, 28, 267.
| Crossref | GoogleScholarGoogle Scholar |
[21] A. P. Kochetkova, L. B. Sveshnikova, V. M. Stepanovich, V. I. Sokol, Sov. J. Coord. Chem. 1982, 8, 281.
[22] V. I. Sokol, M. A. Porai-Koshits, A. P. Kochetkova, L. B. Sveshnikova, Sov. J. Coord. Chem. 1984, 10, 461.
[23] E. Galdecka, Z. Galdecki, F. P. Pruchnik, P. Jakimowciz, Trans. Met. Chem. 2000, 25, 315.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjtVentbY%3D&md5=c435f849e051bc5dfc2b163c999fe331CAS |
[24] C. A. Crawford, J. H. Matonic, J. C. Huffman, K. Folting, K. R. Dunbar, G. Christou, Inorg. Chem. 1997, 36, 2361.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXivFSjtLY%3D&md5=e8a280369679f8096d5d66fccd90fd10CAS | 11669872PubMed |
[25] C. A. Crawford, J. H. Matonic, W. E. Streib, J. C. Huffman, K. R. Dunbar, G. Christou, Inorg. Chem. 1993, 32, 3125.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXkvVCmtLk%3D&md5=1dc5bca6fba35cab04418cc3b8022336CAS |
[26] M. Calligaris, L. Campana, G. Mestroni, M. Tornatore, E. Alessio, Inorg. Chim. Acta 1987, 127, 103.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXit1Khtb8%3D&md5=3b57ba9b94505bab2b02b7dbb243a4ddCAS |
[27] T. Glowaik, H. Pasternak, Acta Crystallogr. 1987, C43, 1036.
[28] T. Glowaik, F. Pruchnik, M. Zuber, Pol. J. Chem. 1991, 65, 1749.
[29] M. A. M. Daniels, N. Mehmet, D. A. Tocher, J. Chem. Soc., Dalton Trans. 1986, 1257.
[30] C. S. Campos-Fernández, X. Ouyang, K. R. Dunbar, Inorg. Chem. 2000, 39, 2432.
| Crossref | GoogleScholarGoogle Scholar | 11196991PubMed |
[31] J. L. Walsh, B. Durham, Inorg. Chem. 1982, 21, 329.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XksFahtA%3D%3D&md5=a0ea8ff998741f16fc5d58ad229b84dfCAS |
[32] A. W. Cordes, B. Durham, W. T. Pennington, B. Kuntz, L. Allen, J. Crystal. Spect. Res. 1992, 22, 699.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXkvFKksQ%3D%3D&md5=44421c3edc8e8d926d3067146f9d97e5CAS |
[33] A. W. Cordes, B. Durham, P. N. Swepston, W. T. Pennington, S. M. Condren, R. Jensen, J. L. Walsh, J. Coord. Chem. 1982, 11, 251.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38Xmt1OqtL4%3D&md5=649ece66509081ead33c5c58127b2f3fCAS |
[34] W. P. Griffith, B. Reddy, A. G. F. Shoair, M. Suriaatmaja, A. J. P. White, D. J. Williams, J. Chem. Soc., Dalton Trans. 1998, 2819.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXlsVSrtbk%3D&md5=a1a3b4a755f7386757dcc8595098a657CAS |
[35] M. A. Masood, B. P. Sullivan, D. J. Hodgson, Inorg. Chem. 1994, 33, 4611.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXmt1Siurc%3D&md5=5e5843373a049a187503c364e06d034dCAS |
[36] R. A. Sheldon, J. K. Kochi, Metal-Catalysed Oxidations of Organic Compounds 1981 (Academic Press: New York).
[37] S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
| Crossref | GoogleScholarGoogle Scholar |
[38] M. Hudlicky, Oxidations in Organic Chemistry 1990, and references therein (American Chemical Society: Washington, DC).
[39] T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXmtlKgsrc%3D&md5=4ce72d39e2852db7f130d0879aaec0daCAS | 11848973PubMed |
[40] A. Dijksman, A. Marino-González, A. M. I. Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am. Chem. Soc. 2001, 123, 6826.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXksVKlt7s%3D&md5=021cf50037079a1e9c3dafca7609b1f4CAS | 11448187PubMed |
[41] W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White, J. Chem. Soc. Chem. Commun. 1987, 1625.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXktlOhuro%3D&md5=01d6c0dd691cbb18a32e95d324960eaaCAS |
[42] K. Vijayasri, J. Rajaram, J. C. Kuriacose, J. Mol. Catal. 1987, 39, 203.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXltleks7Y%3D&md5=382bbe6c4c9966228c84a9eb2fadab7dCAS |
[43] S. Giddings, A. Mills, J. Org. Chem. 1988, 53, 1103.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXhtFWmu7g%3D&md5=0a68802e3cb31d3b7b2ece5bd10c6ed2CAS |
[44] A. J. Bailey, W. P. Griffith, S. I. Mostafa, P. A. Sherwood, Inorg. Chem. 1993, 32, 268.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXht1ektb8%3D&md5=2da06903726444efce54c465194a6752CAS |
[45] W.-H. Fung, W.-Y. Yu, C.-M. Che, J. Org. Chem. 1998, 63, 2873.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXislSgsrs%3D&md5=059e740c2e48008b2e472faa78af4f0cCAS |
[46] S. Kanemoto, K. Oshima, S. Matsubara, K. Takai, H. Nozaki, Tetrahedron Lett. 1983, 24, 2185.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXkvVOgsr0%3D&md5=9556847f10fd14b638ca57737176217dCAS |
[47] M. Tanaka, T.-A. Kobayashi, T. Sakakura, Angew. Chem. 1984, 96, 519.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXkslWrs7o%3D&md5=3a0c6f23b02b7d024b8e42637e537ef5CAS |
[48] B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXktVKmsb4%3D&md5=b43773a94195fe4441f57f76e413766eCAS |
[49] H. Lebel, M. Davi, Adv. Synth. Catal. 2008, 350, 2352.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlOjs7rN&md5=932e722b7b0f1f7266f4aad0eba792ebCAS |
[50] V. B. Sharma, S. L. Jain, B. Sain, Catal. Lett. 2004, 98, 141.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXptlynsLg%3D&md5=03b5e976a9154b3a3bedbe9fe8b8523dCAS |
[51] S. L. Jain, J. K. Joseph, F. E. Kühn, O. Reiser, Adv. Synth. Catal. 2009, 351, 230.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhvVWkt7k%3D&md5=375a8e4ee96744da41e56c7f3f108786CAS |
[52] A. M. Santos, F. M. Pedro, A. A. Yogalekar, I. S. Lucas, C. C. Romão, F. E. Kühn, Chem. Eur. J. 2004, 10, 6313.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtFajsbjE&md5=0b937ecbf275070e3756bbda370df95bCAS |
[53] G. A. Mirafzal, G. Cheng, L. K. Woo, J. Am. Chem. Soc. 2002, 124, 176.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXovF2rtbc%3D&md5=26aeccd9a4ed27c980964712fc1d185fCAS | 11782161PubMed |
[54] F. E. Kühn, A. M. Santos, Mini-Reviews in Org. Chem. 2004, 1, 55.
| Crossref | GoogleScholarGoogle Scholar |
[55] O. Fujimura, T. Honma, Tetrahedron Lett. 1998, 39, 625.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXptVOhsg%3D%3D&md5=e0bed05228823ac680321bc2b2d626fcCAS |
[56] W. A. Herrmann, M. Wang, Angew. Chem. Int. Ed. Engl. 1991, 12, 30.
[57] W. A. Herrmann, P. W. Roesky, M. Wang, W. Scherer, Organometallics 1994, 13, 4531.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXntVSitLc%3D&md5=78b5a8ae4f1c2e76eee55f0f4209d059CAS |
[58] A. Sinha, P. Daw, S. M. W. Rahaman, B. Saha, J. K. Bera, J. Organomet. Chem. 2011, 696, 1248.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjsFarurY%3D&md5=d0911d17606d67ce33376bb8da9bf551CAS |
[59] G. Pimblett, C. D. Garner, W. Clegg, J. Chem. Soc., Dalton Trans. 1986, 1257.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XmtlOhtbY%3D&md5=b88becbfd9d275d765caa59261bcfd29CAS |
[60] W. J. Klemperer, B. Zhong, Inorg. Chem. 1993, 32, 5821.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXksVCksA%3D%3D&md5=c0a16171eed11f7d15202cafa4fbc749CAS |
[61] SAINT+ software for CCD diffractometers 2000 (Bruker AXS: Madison, WI).
[62] G. M. Sheldrick, SADABS Program for Correction of Area Detector Data 1999 (University of Göttingen: Göttingen).
[63] SHELXTL Package v. 6.10 2000 (Bruker AXS: Madison, WI); G. M. Sheldrick, SHELXS-86 and SHELXL-97 1997 (University of Göttingen: Göttingen).
[64] A. L. Spek, PLATON 2001 (University of Utrecht: Utrecht).
[65] L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXnt1KgsLg%3D&md5=014fea354b0cf08dd89b4c674f7abf7dCAS |