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Synthesis 2014; 46(03): 281-289
DOI: 10.1055/s-0033-1338579
DOI: 10.1055/s-0033-1338579
short review
Metal-Catalyzed Cross-Coupling Reactions of Halomaleic Anhydrides and Halomaleimides: Synthesis of Structurally Interesting and Biologically Important Natural and Unnatural Products
Further Information
Publication History
Received: 31 October 2013
Accepted after revision: 06 December 2013
Publication Date:
02 January 2014 (online)
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Abstract
This brief review presents a concise literature account of the metal-catalyzed cross-coupling reactions of halomaleic anhydrides and halomaleimides leading to significant synthetic and natural products. Metal-catalyzed Heck, Suzuki–Miyaura, Stille–Migita, Negishi, Hiyama, and Sonogashira cross-coupling reactions with palladium as the key element are discussed. The metal-catalyzed exchange of a vinylic leaving group by a carbon nucleophile, the SNV reaction, gives a diverse range of bioactive natural and unnatural products.
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References
- 1a Putri SP, Kinoshita H, Ihara F, Igarashi Y, Nihira T. J. Nat. Prod. 2009; 72: 1544
- 1b Chen X, Zheng Y, Shen Y. Chem. Rev. 2007; 107: 1777 ; and references cited therein
- 1c Felthouse TR, Burnett JC, Horrell B, Mummey MJ, Kuo Y.-J. Maleic Anhydride, Maleic Acid, and Fumaric Acid . In Kirk-Othmer Encyclopedia of Chemical Technology . Vol. 15. John Wiley; New York: 2001: 1-49
- 1d Lin K.-F, Lin J.-S, Cheng C.-H. Polymer 1996; 37: 4729
- 2 http://nobelprize.org/nobel_prizes/chemistry/laureates/2010/.
- 3a Li H, Johansson Seechurn CC. C, Colacot TJ. ACS Catal. 2012; 2: 1147
- 3b Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 3c Bolm C. Org. Lett. 2012; 14: 2925
-
3d Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417 ; and references cited therein
-
4a Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177
- 4b Nicolaou KC, Chen JS. Classics in Total Synthesis . Wiley-VCH; Weinheim: 2011
- 4c Nicolaou KC, Snyder SA. Classics in Total Synthesis II . Wiley-VCH; Weinheim: 2003
- 5a de Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions . Wiley-VCH; Weinheim: 2004
- 5b Negishi E, de Meijere A. Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley; New York: 2002
-
6a Slade RM, Branchaud BP. J. Org. Chem. 1998; 63: 3544
- 6b Kar A, Argade NP. J. Org. Chem. 2002; 67: 7131
- 7a Adlington RM, Baldwin JE, Cox RJ, Pritchard GJ. Synlett 2002; 820
- 7b Baldwin JE, Adlington RM, Roussi F, Bulger PG, Marquez R, Mayweg AV. W. Tetrahedron 2001; 57: 7409
- 7c Baldwin JE, Beyeler A, Cox RJ, Keats C, Pritchard GJ, Adlington RM, Watkin DJ. Tetrahedron 1999; 55: 7363
- 8 Shen L, Prouty C, Conway BR, Westover L, Xu JZ, Look RA, Chen X, Beavers MP, Roberts J, Murray WV, Demarest KT, Kuo G.-H. Bioorg. Med. Chem. 2004; 12: 1239
- 9 O’Neill DJ, Shen L, Prouty C, Conway BR, Westover L, Xu JZ, Zhang H.-C, Maryanoff BE, Murray WV, Demarest KT, Kuo G.-H. Bioorg. Med. Chem. 2004; 12: 3167
- 10 Sellès P. Org. Lett. 2005; 7: 605
- 11 Dubernet M, Caubert V, Guillard J, Viaud-Massuard M.-C. Tetrahedron 2005; 61: 4585
- 12a Bourderioux A, Routier S, Bénéteau V, Mérour J.-Y. Tetrahedron Lett. 2005; 46: 6071
- 12b Bourderioux A, Ouach A, Bénéteau V, Mérour J.-Y, Routier S. Synthesis 2010; 783
- 13 Shorunov SV, Krayushkin MM, Stoyanovich FM, Irie M. Russ. J. Org. Chem. 2006; 42: 1490
- 14a Burtoloso AC. B, Garcia AL. L, Miranda KC, Correia CR. D. Synlett 2006; 3145
- 14b Canto K, da Silva Ribeiro R, Biajoli AF. P, Correia CR. D. Eur. J. Org. Chem. 2013; 8004
- 15a Stewart SG, Polomska ME, Lim RW. Tetrahedron Lett. 2007; 48: 2241
- 15b Stewart SG, Ho LA, Polomska ME, Percival AT, Yeoh GC. T. ChemMedChem 2009; 4: 1657
- 16 Yahyaoui AE, Félix G, Heynderickx A, Moustrou C, Samat A. Tetrahedron 2007; 63: 9482
- 17 Roshchin AI, Polunin EV. Mendeleev Commun. 2008; 18: 332
- 18 Cheng C.-F, Lai Z.-C, Lee Y.-J. Tetrahedron 2008; 64: 4347
- 19 Pews-Davtyan A, Tillack A, Ortinau S, Rolfs A, Beller M. Org. Biomol. Chem. 2008; 6: 992
- 20 Brennführer A, Neumann H, Pews-Davtyan A, Beller M. Eur. J. Org. Chem. 2009; 38
- 21 Bouissane L, Sestelo JP, Sarandeses LA. Org. Lett. 2009; 11: 1285
- 22a Roshchin AI, Kuznetsov YV, Polunin EV. Russ. Chem. Bull. 2007; 56: 509
- 22b Roshchin AI. Tetrahedron Lett. 2010; 51: 3633
- 23 Banwell MG, Jones MT, Loong DT. J, Lupton DW, Pinkerton DM, Ray JK, Willis AC. Tetrahedron 2010; 66: 9252
- 24 Awuah E, Capretta A. J. Org. Chem. 2011; 76: 3122
- 25 Deore PS, Argade NP. J. Org. Chem. 2012; 77: 739
- 26 Souffrin A, Croix C, Viaud-Massuard M.-C. Eur. J. Org. Chem. 2012; 2499
- 27 Izgu EC, Hoye TR. Tetrahedron Lett. 2012; 53: 4938
- 28 Waghray D, Dehaen W. Org. Lett. 2013; 15: 2910
- 29 Ambrogi M, Ciogli A, Mancinelli M, Ranieri S, Mazzanti A. J. Org. Chem. 2013; 78: 3709