Abstract
Rare-earth metal catalyzed hydrosilylation of alkenes has emerged as a powerful and selective strategy for the synthesis of organosilanes. This transformation can offer distinctive catalytic sequences and reaction patterns from other catalysts because of the high electropositivity and lack of oxidative-addition process of rare-earth metal. This review summarizes the rare-earth metal catalysts for hydrosilylation of alkene according to the type of ligands. The synthesis and structure of rare-earth metal catalysts, the substrate scope as well as some preliminary structure-activity relationship and mechanism are discussed.
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Ojima I, Li Z, Zhu J. Recent advances in the hydrosilylation and related reactions. In: Rappoport Z, Apeloig Y, Eds. The Chemistry of Organic Silicon Compounds. Vol. 2. New York: Wiley, 1998. 1687–1792
Marciniec B, Maciejewski H, Pietraszuk C, Pawluć P. Part I. Hydrosilylation of carbon-carbon multiple bonds in synthesis of molecular organosilicon compounds. In: Marciniec B, Ed. Hydrosilylation a Comprehensive Review on Recent Advances. Berlin: Springer, 2009. 3–51
Troegel D, Stohrer J. Coord Chem Rev, 2011, 255: 1440–1459
Nakajima Y, Shimada S. RSC Adv, 2015, 5: 20603–20616
Du X, Huang Z. ACS Catal, 2017, 7: 1227–1243
Sun J, Deng L. ACS Catal, 2016, 6: 290–300
Zaranek M, Pawluc P. ACS Catal, 2018, 8: 9865–9876
Karstedt BD. Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes. U S. Patent 3 775 452, 1973
Speier JL, Webster JA, Barnes GH. J Am Chem Soc, 1957, 79: 974–979
Lappert MF, Scott FPA. J Organomet Chem, 1995, 492: C11–C13
Lewis LN, Colborn RE, Grade H, Bryant GL, Sumpter CA, Scott RA. Organometallics, 1995, 14: 2202–2213
Evans WJ. Inorg Chem, 2007, 46: 3435–3449
Edelmann FT. Complexes of group 3 and lanthanide elements. In: Mingos DMP, Crabtree RH, Eds. Comprehensive Organometallic Chemistry III. Oxford: Elsevier, 2007. 1–190
Anwander R. Principles in Organolanthanide Chemistry. Berlin Heidelberg: Springer, 1999. 3
Cui D, Edelmann FT, Hultzsch KC, Jenter J, Li T, Liu B, Reznichenko AL, Roesky PW, Wang B, Yang Y, Zhang Z. Molecular Catalysis of Rare-Earth Elements. Berlin: Springer, 2010
Molander GA, Romero JAC. Chem Rev, 2002, 102: 2161–2186
Hong S, Marks TJ. Acc Chem Res, 2004, 37: 673–686
Weiss CJ, Marks TJ. Dalton Trans, 2010, 39: 6576–6588
Trifonov AA, Basalov IV, Kissel AA. Dalton Trans, 2016, 45: 19172–19193
Trifonov AA. Russ Chem Rev, 2007, 76: 1122–1144
Nishiura M, Guo F, Hou Z. Acc Chem Res, 2015, 48: 2209–2220
Gromada J, Carpentier JF, Mortreux A. Coord Chem Rev, 2004, 248: 397–410
Eisenstein O, Jean Y. J Am Chem Soc, 1985, 107: 1177–1186
Scherer W, McGrady GS. Angew Chem Int Ed, 2004, 43: 1782–1806
Burger BJ, Thompson ME, Cotter WD, Bercaw JE. J Am Chem Soc, 1990, 112: 1566–1577
Ephritikhine M. Chem Rev, 1997, 97: 2193–2242
White JW. Organosilicon compounds for industrial applications. In: Auner N, Weis J, Eds. Organosilicon Chemistry VI: From Molecules to Materials. Weinheim: Wiley, 2005. 602–610
Chalk AJ, Harrod JF. J Am Chem Soc, 1965, 87: 16–21
A. Schroeder M, S. Wrighton M. J Organomet Chem, 1977, 128: 345–358
Fu PF, Brard L, Li Y, Marks TJ. J Am Chem Soc, 1995, 117: 7157–7168
Molander GA, Julius M. J Org Chem, 1992, 57: 6347–6351
Hou Z, Zhang Y, Tardif O, Wakatsuki Y. J Am Chem Soc, 2001, 123: 9216–9217
Zhan G, Teng HL, Luo Y, Lou SJ, Nishiura M, Hou Z. Angew Chem Int Ed, 2018, 57: 12342–12346
Horino Y, Livinghouse T. Organometallics, 2004, 23: 12–14
Konkol M, Kondracka M, Voth P, Spaniol TP, Okuda J. Organometallics, 2008, 27: 3774–3784
Rastätter M, Zulys A, Roesky PW. Chem Commun, 2006, 105: 874
Rastätter M, Zulys A, Roesky PW. Chem Eur J, 2007, 13: 3606–3616
Ruspic C, Spielmann J, Harder S. Inorg Chem, 2007, 46: 5320–5326
Lyubov DM, Bubnov AM, Fukin GK, Dolgushin FM, Antipin MY, Pelcé O, Schappacher M, Guillaume SM, Trifonov AA. Eur J Inorg Chem, 2008, 2008(12): 2090–2098
Trifonov AA, Skvortsov GG, Lyubov DM, Skorodumova NA, Fukin GK, Baranov EV, Glushakova VN. Chem Eur J, 2006, 12: 5320–5327
Ohashi M, Konkol M, Del Rosal I, Poteau R, Maron L, Okuda J. J Am Chem Soc, 2008, 130: 6920–6921
Ge S, Meetsma A, Hessen B. Organometallics, 2008, 27: 3131–3135
Bambirra S, van Leusen D, Meetsma A, Hessen B, Teuben JH. Chem Commun, 2003, 522–523
Trambitas AG, Panda TK, Jenter J, Roesky PW, Daniliuc C, Hrib CG, Jones PG, Tamm M. Inorg Chem, 2010, 49: 2435–2446
Levine DS, Tilley TD, Andersen RA. Chem Commun, 2017, 53: 11881–11884
Shi Y, Li J, Cui C. Dalton Trans, 2017, 46: 10957–10962
Gountchev TI, Tilley TD. Organometallics, 1999, 18: 5661–5667
Li J, Zhao C, Liu J, Huang H, Wang F, Xu X, Cui C. Inorg Chem, 2016, 55: 9105–9111
Liu J, Chen W, Li J, Cui C. ACS Catal, 2018, 8: 2230–2235
Elvidge BR, Arndt S, Spaniol TP, Okuda J. Dalton Trans, 2006, 102: 890–901
Gribkov DV, Hampel F, Hultzsch KC. Eur J Inorg Chem, 2004, 2004 (20): 4091–4101
Konkol M, Spaniol TP, Kondracka M, Okuda J. Dalton Trans, 2007, 95: 4095
Abinet E, Spaniol TP, Okuda J. Chem Asian J, 2011, 6: 389–391
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This work was supported by the National Natural Science Foundation of China (21632006, 21472098) and Natural Science Foundation of Tianjin (16JCQNJC05800).
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Liu, D., Liu, B., Pan, Z. et al. Rare-earth metal catalysts for alkene hydrosilylation. Sci. China Chem. 62, 571–582 (2019). https://doi.org/10.1007/s11426-018-9403-7
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DOI: https://doi.org/10.1007/s11426-018-9403-7