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Synlett 2013; 24(20): 2624-2628
DOI: 10.1055/s-0033-1338981
DOI: 10.1055/s-0033-1338981
synpacts
Multidentate Halogen-Bond Donors as Lewis Acidic Activators or Catalysts in Halide Abstraction Reactions
Further Information
Publication History
Received: 07 August 2013
Accepted after revision: 06 September 2013
Publication Date:
28 October 2013 (online)
Abstract
Although halogen bonds share many similarities with hydrogen bonds, they have so far found virtually no application in organic synthesis. This account summarizes our efforts to use multidentate halogen-bond donors (halogen-based Lewis acids) in formal halide abstraction reactions. Following a first proof-of-principle study, we recently reported the first halogen-bond-based organocatalytic carbon–carbon bond-forming reaction.
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References
- 1 Jeffrey GA. An Introduction to Hydrogen Bonding . Oxford University Press; Oxford: 1997
- 3a Hassel O, Rømming C. Q. Rev. Chem. Soc. 1962; 16: 1
- 3b Bent HA. Chem. Rev. 1968; 68: 587
- 3c Weiss R, Miess G.-E, Haller A, Reinhardt W. Angew. Chem., Int. Ed. Engl. 1986; 25: 103
- 3d Weiss R, Rechinger M, Hampel F. Angew. Chem., Int. Ed. Engl. 1994; 33: 893
- 3e Legon AC. Angew. Chem. Int. Ed. 1999; 38: 2686
- 4a Metrangolo P, Meyer F, Pilati T, Resnati G, Terraneo G. Angew. Chem. Int. Ed. 2008; 47: 6114
- 4b Fourmigué M. Curr. Opin. Solid State Mater. Sci. 2009; 13: 36
- 4c Legon AC. Phys. Chem. Chem. Phys. 2010; 12: 7736
- 4d Lu Y, Wang Y, Zhu W. Phys. Chem. Chem. Phys. 2010; 12: 4543
- 4e Definition of the halogen bond by IUPAC: Desiraju GR, Ho PS, Kloo L, Legon AC, Marquardt R, Metrangolo P, Politzer P, Resnati G, Rissanen K. Pure Appl. Chem. 2013; 85: 1711
- 5a Hassel O. Angew. Chem., Int. Ed. Engl. 1970; 82: 821
- 5b Reed AE, Weinhold F, Weiss R, Macheleid J. J. Phys. Chem. A 1985; 89: 2688
- 5c Ramasubbu N, Parthasarathy R, Murray-Rust P. J. Am. Chem. Soc. 1986; 108: 4308
- 5d Karpfen A. Theor. Chem. Acc. 2003; 110: 1
- 6a Politzer P, Murray JS, Clark T. Phys. Chem. Chem. Phys. 2010; 12: 7748
- 6b Clark T. WIREs Comput. Mol. Sci. 2013; 3: 13
- 7a Huber SM, Jimenez-Izal E, Ugalde JM, Infante I. Chem. Commun. 2012; 48: 7708
- 7b Huber SM, Scanlon JD, Jimenez-Izal E, Ugalde JM, Infante I. Phys. Chem. Chem. Phys. 2013; 15: 10350
- 7c Stone AJ. J. Am. Chem. Soc. 2013; 135: 7005
- 8a Rissanen K. CrystEngComm 2008; 10: 1107
- 8b Brammer L, Espallargas GM, Libri S. CrystEngComm 2008; 10: 1712
- 8c Metrangolo P, Pilati T, Terraneo G, Biella S, Resnati G. CrystEngComm 2009; 11: 1187
- 8d Cavallo G, Metrangolo P, Pilati T, Resnati G, Sansotera M, Terraneo G. Chem. Soc. Rev. 2010; 39: 3772
- 9a Benesi HA, Hildebrand JH. J. Am. Chem. Soc. 1949; 71: 2703
- 9b Di Paolo T, Sandorfy C. Can. J. Chem. 1974; 52: 3612
- 10a Erdélyi M. Chem. Soc. Rev. 2012; 41: 3547
- 10b Beale TM, Chudzinski MG, Sarwar MG, Taylor MS. Chem. Soc. Rev. 2013; 42: 1667
- 11a Metrangolo P, Panzeri W, Recupero F, Resnati G. J. Fluorine Chem. 2002; 114: 27
- 11b Libri S, Jasim NA, Perutz RN, Brammer L. J. Am. Chem. Soc. 2008; 130: 7842
- 11c Sarwar MG, Dragisić B, Salsberg LJ, Gouliaras C, Taylor MS. J. Am. Chem. Soc. 2010; 132: 1646
- 11d Cametti M, Raatikainen K, Metrangolo P, Pilati T, Terraneoa G, Resnati G. Org. Biomol. Chem. 2012; 10: 1329
- 11e Sarwar MG, Dragisić B, Dimitrijević E, Taylor MS. Chem. Eur. J. 2013; 19: 2050
- 12a Vargas Jentzsch A, Emery D, Mareda J, Metrangolo P, Resnati G, Matile S. Angew. Chem. Int. Ed. 2011; 50: 11675
- 12b Vargas Jentzsch A, Emery D, Mareda J, Nayak SK, Metrangolo P, Resnati G, Sakai N, Matile S. Nat. Commun. 2012; 3: 905
- 12c Vargas Jentzsch A, Matile S. J. Am. Chem. Soc. 2013; 135: 5302
- 13a Kilah NL, Wise MD, Serpell CJ, Thompson AL, White NG, Christensen KE, Beer PD. J. Am. Chem. Soc. 2010; 132: 11893
- 13b Serpell CJ, Kilah NL, Costa PJ, Félix V, Beer PD. Angew. Chem. Int. Ed. 2010; 49: 5322
- 13c Caballero A, Zapata F, White NG, Costa PJ, Félix V, Beer PD. Angew. Chem. Int. Ed. 2012; 51: 1876
- 14a Mele A, Metrangolo P, Neukirch H, Pilati T, Resnati G. J. Am. Chem. Soc. 2005; 127: 14972
- 14b Sarwar MG, Dragisic B, Sagoo S, Taylor MS. Angew. Chem. Int. Ed. 2010; 49: 1674
- 14c Dimitrijević E, Kvak P, Taylor MS. Chem. Commun. 2010; 46: 9025
- 14d Caballero A, White NG, Beer PD. Angew. Chem. Int. Ed. 2011; 50: 1845
- 14e Zapata F, Caballero A, White NG, Claridge TD. W, Costa PJ, Félix V, Beer PD. J. Am. Chem. Soc. 2012; 134: 11533
- 15a Bruckmann A, Pena MA, Bolm C. Synlett 2008; 900
- 15b Coulembier O, Meyer F, Dubois P. Polym. Chem. 2010; 1: 434
- 16a Togo H, Iida S. Synlett 2006; 2159
- 16b Jereb M, Vrazic D, Zupan M. Tetrahedron 2011; 67: 1355
- 17a Zhang Z, Schreiner PR. Chem. Soc. Rev. 2009; 38: 1187
- 17b Beckendorf S, Asmus S, Mancheño OG. ChemCatChem 2012; 4: 926
- 17c Mahlau M, List B. Angew. Chem. Int. Ed. 2013; 52: 518
- 17d Brak K, Jacobsen EN. Angew. Chem. Int. Ed. 2013; 52: 534
- 18 Dang TT, Boeck F, Hintermann L. J. Org. Chem. 2011; 76: 9353
- 19a Walter SM, Kniep F, Herdtweck E, Huber SM. Angew. Chem. Int. Ed. 2011; 50: 7187
- 19b Walter SM, Kniep F, Rout L, Schmidtchen FP, Herdtweck E, Huber SM. J. Am. Chem. Soc. 2012; 134: 8507
- 19c Kniep F, Walter SM, Herdtweck E, Huber SM. Chem. Eur. J. 2012; 18: 1306
- 19d Kniep F, Rout L, Walter SM, Bensch HK. V, Jungbauer SH, Herdtweck E, Huber SM. Chem. Commun. 2012; 48: 9299
- 20 Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, van de Streek J. J. Appl. Cryst. 2006; 39: 453
- 21 Bondi A. J. Phys. Chem. 1964; 68: 441
- 22 Walter SM, Jungbauer SH, Kniep F, Schindler S, Herdtweck E, Huber SM. J. Fluorine Chem. 2013; 150: 14
- 23 Kniep F, Jungbauer SH, Zhang Q, Walter SM, Schindler S, Schnapperelle I, Herdtweck E, Huber SM. Angew. Chem. Int. Ed. 2013; 52: 7028
- 24 Reisman SA, Doyle AG, Jacobsen EN. J. Am. Chem. Soc. 2008; 130: 7198
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