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Jiang, X. et al.: 2021 Science of Synthesis: Knowledge Updates 2020/3 DOI: 10.1055/sos-SD-114-00314
Knowledge Updates 2020/3

14.10.3 Selenopyrylium and Benzoselenopyrylium Salts (Update 2020)

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Book

Editors: Jiang, X.; Marschner, C.; Oestreich, M.; Wang, M.

Authors: An, K.; Arisetti, N.; Cheng, B.; Gao, W.-C.; He, W.; Jiang, B.; Krause, N.; Lu, J.; Marschner, C.; Shao, L.; Shi, T.; Tan, Q.; Tian, J.; Wang, T.; Wang, Z.; Wei, W.; Weinert, C.; Zhang, H.-H.; Zhang, Q.; Zhao, X.; Zhu, C.-F.

Title: Knowledge Updates 2020/3

Print ISBN: 9783132435643; Online ISBN: 9783132435667; Book DOI: 10.1055/b000000104

1st edition © 2020 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

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: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G.; Nevado, C.; Trost, B. M.; You, S.

Type: Multivolume Edition

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Abstract

This chapter is an update to the earlier Science of Synthesis chapter (Section 14.10) describing methods for the synthesis of selenopyrylium and benzoselenopyrylium salts. It focuses on the literature published in the period 2001–2019.

Key words

selenopyrylium salts - benzoselenopyrylium salts - selenium - aromatization - substitution - dehydration - condensation reactions - ion-exchange reactions - coupling reactions - oxidation - dearomatization
 
  • 1 Sashida H.. Mini-Rev. Org. Chem 2007; 4: 105
  • 2 Guziec Jr. F. S., Guziec L. J., Comprehensive Heterocyclic Chemistry III. Katritzky A. R., Ramsden C. A., Scriven E. F. V., Taylor R. J. K.. Elsevier; Oxford 2008. 7, p 955.
    Google Scholar
  • 3 Sashida H., Kaname M., Ohyanagi K., Minoura M.. Tetrahedron 2012; 68: 10 502
  • 4 Ouchi A., Ando W., Oba M.. Patai’s Chemistry of Functional Groups: Organic Selenium and Tellurium. Wiley; New York 2013
    Google Scholar
  • 5 Fernández-Lodeiro J., Pinatto-Botelho M. F., Soares-Paulino A. A., Gonçalves A. C., Sousa B. A., Princival C., Santos A. A. D.. Dyes Pigm 2014; 110, 28
  • 6 Braga A. L., Rafique J.. Patai’s Chemistry of Functional Groups: Organic Selenium and Tellurium. Wiley; New York 2014
    Google Scholar
  • 7 Hales J. M., Barlow S., Kim H., Mukhopadhyay S., Brédas J.-L., Perry J. W., Marder S. R.. Chem. Mater 2014; 26, 549
  • 8 Logan M. E., Lang M. A., Detty M. R.. Patai’s Chemistry of Functional Groups: Organic Selenium and Tellurium. Wiley; New York 2014
    Google Scholar
  • 9 Elsherbini M., Hamama W. S., Zoorob H. H.. Coord. Chem. Rev 2017; 330: 110
  • 10 Wang Z.-X., von Ragué , Schleyer P.. Helv. Chim. Acta 2001; 84: 1578
  • 11 Priyakumar U. D., Sastry G. N.. Proc. - Indian Acad. Sci., Chem. Sci 2003; 115: 49
  • 12 Kassaee M. Z., Jalalimanesh N., Musavi S. M.. J. Mol. Struct.: THEOCHEM 2007; 816: 153
  • 13 Ebrahimi A. A., Ghiasi R., Foroutan-Nejad C.. J. Mol. Struct.: THEOCHEM 2010; 941: 47
  • 14 Quiñonero D.. Molecules 2015; 20: 11 632
  • 15 Báez-Grez R., Rabanal-León W. A., Alvarez-Thon L., Ruiz L., Tiznado W., Pino-Rios R.. J. Phys. Org. Chem 2019; 32: e3823
  • 16 Hales J. M., Matichak J., Barlow S., Ohira S., Yesudas K., Brédas J.-L., Perry J. W., Marder S. R.. Science (Washington, D. C.) 2010; 327: 1485
  • 17 Ebert S. P., Wetzel B., Myette R. L., Conseil G., Cole S. P. C., Sawada G. A., Loo T. W., Bartlett M. C., Clarke D. M., Detty M. R.. J. Med. Chem 2012; 55: 4683
  • 18 Brennan N. K., Hall J. P., Davies S. R., Gollnick S. O., Oseroff A. R., Gibson S. L., Hilf R., Detty M. R.. J. Med. Chem 2002; 45: 5123
  • 19 Detty M. R., Gibson S. L., Hilf R.. Bioorg. Med. Chem 2004; 12: 2589
  • 20 McKnight R. E., Ye M., Ohulchanskyy T. Y., Sahabi S., Wetzel B. R., Wagner S. J., Skripchenko A., Detty M. R.. Bioorg. Med. Chem 2007; 15: 4406
  • 21 Sawada G. A., Raub T. J., Higgins J. W., Brennan N. K., Moore T. M., Tombline G., Detty M. R.. Bioorg. Med. Chem 2008; 16: 9745
  • 22 Barlow S., Brédas J.-L., Getmanenko Y. A., Gieseking R. L., Hales J. M., Kim H., Marder S. R., Perry J. W., Risko C., Zhang Y.. Mater. Horiz 2014; 1: 577
  • 23 Getmanenko Y. A., Allen T. G., Kim H., Hales J. M., Sandhu B., Fonari M. S., Suponitsky K. Yu., Zhang Y., Khrustalev V. N., Matichak J. D., Timofeeva T. V., Barlow S., Chi S.-H., Perry J. W., Marder S. R.. Adv. Funct. Mater 2018; 28: 1 804 073
  • 24 Haque S. A., Nelson J.. Science (Washington, D. C.) 2010; 327: 1466
  • 25 Davydenko I., Benis S., Shiring S. B., Simon J., Sharma R., Allen T. G., Chi S.-H., Zhang Q., Getmanenko Y. A., Parker T. C., Perry J. W., Brédas J.-L., Hagan D. J., Stryland E. W. V., Barlow S., Marder S. R.. J. Mater. Chem. C 2018; 6: 3613
  • 26 Barachati F., Simon J., Getmanenko Y. A., Barlow S., Marder S. R., Kéna-Cohen S.. ACS Photonics 2018; 5: 119
  • 27 Harmsen S., Bedics M. A., Wall M. A., Huang R., Detty M. R., Kircher M. F.. Nat. Commun 2015; 6: 6570
  • 28 Bedics M. A., Mulhern K. R., Watson D. F., Detty M. R.. J. Org. Chem 2013; 78: 8885
  • 29 Detty M. R., Young D. N., Williams A. J.. J. Org. Chem 1995; 60: 6631
  • 30 Sashida H., Ohyanagi K., Minoura M., Akiba K.-y.. J. Chem. Soc., Perkin Trans. 1 2002; 606
  • 31 Nagahora N., Kushida T., Shioji K., Okuma K.. Organometallics 2019; 38: 1800
  • 32 Sashida H., Yoshida M., Minamida H., Teranishi M.. J. Heterocycl. Chem 2002; 39: 405
  • 33 Sashida H., Ohyanagi K.. Chem. Pharm. Bull 2004; 52: 57
  • 34 Sashida H., Ohyanagi K.. Chem. Pharm. Bull 2005; 53: 60