Abstract
A novel diphosphino-functionalized MCM-41 anchored rhodium complex [MCM-41-2P-RhCl(PPh3)] was conveniently synthesized by the reaction of diphosphino-functionalized MCM-41 (MCM-41-2P) with RhCl(PPh3)3. It was found that this rhodium complex is an efficient catalyst for the hydrothiolation of terminal alkynes with thiols and can be recovered and recycled by a simple filtration of the reaction solution and used for at least ten consecutive trials without any decreases in activity.
Graphical Abstract
The diphosphino-functionalized MCM-41 anchored rhodium complex [MCM-41-2P-RhCl(PPh3)] is an efficient catalyst for the hydrothiolation of terminal alkynes with thiols and can be recovered and recycled by a simple filtration of the reaction solution and used for at least ten consecutive trials without any decreases in activity.
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References
Bayon JC, Claver C, Masdeu-Bulto AM (1999) Coord Chem Rev 193:73
Hu R, Zha L, Cai M (2010) Catal Commun 11:563
Backvall J-E, Ericsson A (1994) J Org Chem 59:5850
Ogawa A, Kawakami J, Mihara M, Ikeda T, Sonoda N, Hirao T (1997) J Am Chem Soc 119:12380
Xiao W-J, Vasapollo G, Alper H (1998) J Org Chem 63:2609
Bratz M, Bullock WH, Overman LE, Takemoto T (1995) J Am Chem Soc 117:5958
Farhat S, Zouev I, Marek I (2004) Tetrahedron 60:1329
Pearson WH, Lee IY, Mi Y, Stoy P (2004) J Org Chem 69:9109
Sabarre A, Love JA (2008) Org Lett 10:3941
Benati L, Capella L, Montevecchi PC, Spagnolo P (1995) J Chem Soc Perkin Trans 1:1035
Kuniyasu H, Ogawa A, Sato K, Ryu I, Kambe N, Sonoda N (1992) J Am Chem Soc 114:5902
Ogawa A, Ikeda T, Kimura K, Hirao T (1999) J Am Chem Soc 121:5108
Cao C, Fraser LR, Love JA (2005) J Am Chem Soc 127:17614
Burling S, Field LD, Messerle BA, Vuong KQ, Turner P (2003) Dalton Trans 4181
Field LD, Messerle BA, Vuong KQ, Turner P (2009) Dalton Trans 3599
Shoai S, Bichler P, Kang B, Buckley H, Love JA (2007) Organometallics 26:5778
Fraser LR, Bird J, Wu Q, Cao C, Patrick BO, Love JA (2007) Organometallics 26:5602
Yang J, Sabarre A, Fraser LR, Patrick BO, Love JA (2009) J Org Chem 74:182
Ananikov VP, Gayduk KA, Orlov NV, Beletskaya IP, Khrustalev VN, Antipin MY (2010) Chem Eur J 16:2063
Weiss CJ, Marks TJ (2010) J Am Chem Soc 132:1053
Poliakoff M, Fitzpatrick JM, Farren TR, Anastas PT (2002) Science 297:807
Kirschnig A, Monenschein H, Wittenberg R (2001) Angew Chem Int Ed 40:650
Leadbeater NE, Marco M (2002) Chem Rev 102:3217
Yin L, Liebscher J (2007) Chem Rev 107:133
Molnar A (2011) Chem Rev 111:2251
Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS (1992) Nature 359:710
Beck JS, Vartuli JC, Roth WJ, Leonowicz ME, Kresge CT, Schmitt KD, Chu CT-W, Olson DH, Sheppard EW, McCullen SB, Higgins JB, Schlenker JL (1992) J Am Chem Soc 114:10834
Zhou W, Thomas JM, Shephard DS, Johnson BFG, Ozkaya D, Maschmeyer T, Bell RG, Ge Q (1998) Science 280:705
Maschmeyer T, Rey F, Sankar G, Thomas JM (1995) Nature 378:159
Liu C-J, Li S-G, Pang W-Q, Che C-M (1997) Chem Commun 65
Shyu S-G, Cheng S-W, Tzou D-L (1999) Chem Commun 2337
Zhao H, Wang Y, Sha J, Cai M (2008) Tetrahedron 64:7517
Merckle C, Blumel J (2005) Top Catal 34:5
Reinhard S, Blumel J (2003) Magn Reson Chem 41:406
Kumar P, Kumar Pandey R, Hegde VR (1999) Synlett 1921
Kanagasabapathy S, Sudalai A, Benicewicz BC (2001) Tetrahedron Lett 42:3791
Acknowledgments
We thank the National Natural Science Foundation of China (Project No. 20862008) and the Natural Science Foundation of Jiangxi Province in China (2008GQH0034, 2010GZH0062) for financial support.
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Zhao, H., Peng, J. & Cai, M. Heterogeneous Hydrothiolation of Alkynes with Thiols Catalyzed by Diphosphino-Functionalized MCM-41 Anchored Rhodium Complex. Catal Lett 142, 138–142 (2012). https://doi.org/10.1007/s10562-011-0732-x
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DOI: https://doi.org/10.1007/s10562-011-0732-x