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Mingli Li 2014-6-7 1
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( stored as THF solutions, blue-green for SmI 2 and yellow-green for YbI 2 ) Deoxygenation Reactions Reductions of Double Bonds Reduction of Halides and Tosylates Alkylations of Ketones by Organic Halides or Organic Sulfonates. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. SmI 2 3
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1 reductive manipulations of functional groups 2 reductive couplings to make C− C bonds 2.1 Barbier–Grignard processes ( the reaction of organic halides with carbonyl compounds ) 2.2 Radical alkene addition reactions 2.3 Ketyl radical alkene addition reactions 2.4 Pinacol coupling processes Two major classes of reactions mediated by samarium(II) iodide 4
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Functional group reduction Procter. D. J. Chem. Rev., Articles ASAP 5
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2.1 Barbier–Grignard processes Panek, J. S. J. Org. Chem. 2011, 76, 9900. Nicolaou, K. C.Angew. Chem., Int. Ed. 2011, 50, 1139. 6
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2.2 Radical alkene addition reactions Molander. G. A. J. Org. Chem., 1997, 62, 7418. Guibe. F. Tetrahedron Lett., 1999, 40, 8557. Procter. D. J. J. Chem. Soc., Perkin Trans. 1, 2000, 681. 7
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2.3 Ketyl radical alkene addition reactions Villar, H.; Guibe ́,F. Tetrahedron Lett. 2002, 43,9517. Guibe ́, F. Tetrahedron Lett. 2007, 48, 8234. 8
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2.4 Pinacol coupling processes Corey, E. J. J. Am. Chem. Soc. 2005, 127, 13813. Cozzi, F.; Siegel, J. S. Org. Biomol. Chem. 2003, 1, 157 9
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Procter, D. J. Tetrahedron Lett. 2009, 50, 3224. Procter, D. J. Tetrahedron 2009, 65, 10816. 3 Cross-Coupling As Part of Sequential and Cascade Reactions 10
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Procter, D. J. Angew. Chem., Int. Ed. 2009, 48, 9315. 11
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Reisman, S. E. J. Am. Chem. Soc. 2011,133, 14964 Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 11764. 12
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Beemelmanns, C.; Reissig, H.-U. Angew. Chem., Int. Ed. 2010, 49, 8021. Beemelmanns, C.; Gross, S.; Reissig, H.-U. Chem. -Eur. J. 2013, 19, 17801. 13
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Breitler, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2013, 52, 11168. 14
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Murphy, G. K.; Wood, J. L. J. Org. Chem. 2013, 78, 477 15
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Inui, M.; Nakazaki, A.; Kobayashi, S. Org. Lett. 2007, 9, 469. 16
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Kilburn, J. D. Org. Lett. 2004, 6, 1943. 17
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Kilburn, J. D. Tetrahedron Lett. 2004, 45, 2223. 18
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Kaki uchi, K. Tetrahedron Lett. 2003, 44, 1963. Luo, Z.; Zhou, B.; Li, Y. Org. Lett. 2012, 14, 2540. 19
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Schwartz, A.; Seger, C. Monatsh. Chem. 2001, 132, 855. 20
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Molander, G. A. J. Org. Chem. 2002, 67, 3459. 21
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St. Jean, D. J. Tetrahedron Lett. 2006, 47, 6225. Molander, G. A. J. Org. Chem. 2001, 66, 4511. 22
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Suzuki, K. Angew. Chem., Int. Ed. 2006, 45, 6294. 23
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Procter, D. J. Org. Biomol. Chem. 2011,9, 5104. 24
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Pattenden, G. Tetrahedron Lett. 2013, 54, 6822. 25
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Many challenges need to be addressed asymmetric SmI2 -mediated cross-coupling reactions the expansion and generalization of the scope of existing reactions the design of new ligands increased mechanistic understanding of the underlying electron transfer processes 26
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