Aitken, R. A. et al.: 2016 Science of Synthesis, 2015/2: Knowledge Updates 2015/2 DOI: 10.1055/sos-SD-135-00123
Knowledge Updates 2015/2

35.3.1.5.7 Synthesis by Substitution of Oxygen Functionalities (Update 2015)

More Information

Book

Editors: Aitken, R. A.; Brønsted Nielsen, M.; Drabowicz, J.; Li, J. J.; Plietker, B.; Wirth, T.

Authors: Banert, K.; Brønsted Nielsen, M.; Cacciarini, M.; Elliott, M.; Grün, A.; Hagen, T.; Helgren, T.; Hennecke, U.; Iskra, J.; Kang, F.-A.; Keglevich, G.; Larsen, M. H.; Li, H.; Mazet, C.; Murphree, S.S.; Nomoto, A.; Ogawa, A.; Reißig, H.-U.; Saleh, B. A.; Singh, F. V. ; Tomé, A. C.; Wirth, T.; Yang, S.-M.; Zimmer, R.

Title: Knowledge Updates 2015/2

Print ISBN: 9783131984616; Online ISBN: 9783131975812; Book DOI: 10.1055/b-003-125870

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

 

Abstract

Iodoalkanes are important synthetic intermediates in organic chemistry. These compounds undergo various reactions such as nucleophilic substitution, elimination, and metal-catalyzed C—C bond-forming reactions. This chapter describes various synthetic approaches available for the generation of C—I bonds from different oxygen functionalities and covers the literature published in the period 2007–2014.

 
  • 1 Trewick S. C., Henshaw T. F., Hausinger R. P., Lindahl T., Sedgwick B. Nature (London) 2002; 419: 174
  • 2 Friestad G. K., Marie J.-C., Deveau A. M. Org. Lett. 2004; 6: 3249
  • 3 Krafft M. E., Seibert K. A., Haxell T. F. N., Hirosawa C. Chem. Commun. (Cambridge) 2005; 5772
  • 4 Zhong M., Robins M. J. J. Org. Chem. 2006; 71: 8901
  • 5 Reinhard R., Schmidt B. F. J. Org. Chem. 1998; 63: 2434
  • 6 Smith T. H., Fujiwara A. N., Henry D. W. J. Med. Chem. 1979; 22: 40
  • 7 Loksha Y. M., El-Badawi M. A., El-Barbary A. A., Pedersen E. B., Nielsen C. Arch. Pharm. (Weinheim, Ger.) 2003; 336: 175
  • 8 DeGraw J. I., Colwell W. T., Crase J., Smith R. L., Piper J. R., Waud W. R., Sirotnak F. M. J. Med. Chem. 1997; 40: 370
  • 9 Andrus M. B., Hicken E. J., Stephens J. C., Bedke D. K. J. Org. Chem. 2005; 70: 9470
  • 10 Liang F., Sadana A. K., Peera A., Chattopadhyay J., Gu Z., Hauge R. H., Billups W. E. Nano Lett. 2004; 4: 1257
  • 11 Yu B., Edstrom W. C., Benach J., Hamuro Y., Weber P. C., Gibney B. R., Hunt J. F. Nature (London) 2006; 439: 879
  • 12 Cao C., Kwon K., Jiang Y. L., Drohat A. C., Stivers J. T. J. Biol. Chem. 2003; 278: 48 012
  • 13 Takahashi K., Kawazoe Y., Sakumi K., Nakabeppu Y., Sekiguchi M. J. Biol. Chem. 1988; 263: 13 490
  • 14 Myers L. C., Wagner G., Verdine G. L. J. Am. Chem. Soc. 1995; 117: 10 749
  • 15 Azhar K. F., Qudrat-e-Khuda M., Zuberi R. J. Chem. Soc. Pak. 2002; 24: 57
  • 16 Schiffmann D., Eder E., Neudecker T., Henschler D. Cancer Lett. 1983; 20: 263
  • 17 Singh F. V., Rehbein J., Wirth T. ChemistryOpen 2012; 1: 245
  • 18 Deligeorgiev T., Kaloyanova S., Lesev N., Vaquero J. J. Ultrason. Sonochem. 2010; 17: 783
  • 19 Bol C. W. J., Friend C. M. Surf. Sci. 1996; 364: L549
  • 20 Zhang X., Liu J., Liu Y., Du Y. Tetrahedron Lett. 2013; 54: 4045
  • 21 Rajendran S., Ramkumar V., Sankararaman S. Organometallics 2011; 30: 1689
  • 22 Sawaguchi M., Hara S., Nakamura Y., Ayuba S., Fukuhara T., Yoneda N. Tetrahedron 2001; 57: 3315
  • 23 Ouellette R. J., Rawn J. D. Organic Chemistry. Elsevier; San Diego 2014 pp 287
  • 24 Uemura S., Fukuzawa S.-I. J. Organomet. Chem. 1984; 268: 223
  • 25 Kanyi C. W., Doetschman D. C., Yang S.-W., Schulte J., Jones B. R. Microporous Mesoporous Mater. 2008; 108: 103
  • 26 Singh F. V., Kumar R., Sharon A., Broder C. K., Howard J. A. K., Goel A., Maulik P. R. J. Mol. Struct. 2006; 782: 55
  • 27 Marton D., Tari M. J. Organomet. Chem. 2000; 612: 78
  • 28 Singh F. V., Wirth T. Synthesis 2012; 44: 1171
  • 29 Someya H., Yorimitsu H., Oshima M. Tetrahedron 2010; 66: 5993
  • 30 Yasuda M., Onishi Y., Ueba M., Miyai T., Baba A. J. Org. Chem. 2001; 66: 7741
  • 31 Yasuda M., Saito T., Ueba M., Baba A. Angew. Chem. Int. Ed. 2004; 43: 1414
  • 32 Harrison G. C., Diehl H. Org. Synth., Coll. Vol. III 1953; 370
  • 33 Voronkov M. G., Trukhina A. A., Vlasova N. N. Russ. J. Org. Chem. (Engl. Transl.) 2002; 38: 1576
  • 34 Iranpoor N., Firouzabadi H., Aghapour G., Vaezzadeh A. R. Tetrahedron 2002; 58: 8689
  • 35 Lasne M.-C., Cairon P., Villemin D. Synth. Commun. 1990; 20: 41
  • 36 Martínez A. G., Villalobos A. C., Ruiz M. O. Synthesis 1988; 58
  • 37 Kanai T., Irifune S., Ishii Y., Ogawa M. Synthesis 1989; 283
  • 38 Alvarez-Manzaneda E. J., Chahboun R., Torres E. C., Alvarez E., Alvarez-Manzaneda R., Haidour A., López J. M. R. Tetrahedron Lett. 2005; 46: 3755
  • 39 Guo L., Liu Y., Wan Y., Wang P. G., Zhao W. Tetrahedron Lett. 2013; 54: 2579
  • 40 Årstad E., Barrett A. G. M., Hopkins B. T., Köbberling J. Org. Lett. 2002; 4: 1975
  • 41 Ranu B. C., Jana R. Eur. J. Org. Chem. 2005; 755
  • 42 Iranpoor N., Firouzabadi H., Jamalian A., Kazemi F. Tetrahedron 2005; 61: 5699
  • 43 Das B., Holla H., Srinivas Y., Chowdhury N., Bandgar B. P. Tetrahedron Lett. 2007; 48: 3201
  • 44 Klein S. M., Zhang C., Jiang Y. L. Tetrahedron Lett. 2008; 49: 2638
  • 45 Zhu Q., Tremblay M. S. Bioorg. Med. Chem. Lett. 2006; 16: 6170
  • 46 Pavan M. V., Lassiani L., Berti F., Stefancich G., Ciogli A., Gasparrini F., Mennuni L., Ferrari F., Escrieut C., Marco E., Makovec F., Fourmy D., Varnavas A. J. Med. Chem. 2011; 54: 5769
  • 47 Dennison P. R., Gibson A., Gray A. I., Patrick G. L. J. Chem. Soc., Perkin Trans. 1 1997; 721
  • 48 Liu Y., Xu Y., Jung S. H., Chae J. Synlett 2012; 23: 2692
  • 49 Coskun T., Conifer C. M., Stevenson L. C., Britovsek G. J. P. Chem.–Eur. J. 2013; 19: 6840
  • 50 Firouzabadi H., Iranpoor N., Hazarkhani H. Tetrahedron Lett. 2002; 43: 7139
  • 51 Mirjafari A., Mohammadpoor-Baltork I., Moghadam M., Tangestaninejad S., Mirkhani V., Khosropour A. R. Tetrahedron Lett. 2010; 51: 3274
  • 52 Mohammadpoor-Baltork I., Moghadam M., Tangestaninejad S., Mirkhani V., Mirjafari A. C. R. Chim. 2011; 13: 1468