Jiang, X. et al.: 2021 Science of Synthesis: Knowledge Updates 2020/3 DOI: 10.1055/sos-SD-114-00215
Knowledge Updates 2020/3

14.7.5 Benzothiopyrylium Salts (Update 2020)

More Information

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

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

 

Abstract

This chapter is an update to the original Science of Synthesis contribution (Section 14.7) describing methods for the synthesis of benzothiopyrylium salts. Although this update also covers new approaches to 1- and 2-benzothiopyrylium salts, most methods developed during recent years have focused on dibenzo[b,e]thiopyrylium salts.

 
  • 1 Zhang F., Wang S.. CN 109 180 638, 2019
  • 2 Li D., Wang S., Lei Z., Sun C., El-Toni A. M., Alhoshan M. S., Fan Y., Zhang F.. Anal. Chem 2019; 91: 4771
  • 3 Kargapolova I. Y., Orlova N. A., Erin K. D., Shelkovnikov V. V.. Russ. J. Org. Chem. (Engl. Transl.) 2016; 52: 37
  • 4 Klein T. R., Bergemann M., Yehia N. A. M., Fanghänel E.. J. Org. Chem 1998; 63: 4626
  • 5 Spencer J., Pfeffer M., DeCian A., Fischer J.. J. Org. Chem 1995; 60: 1005
  • 6 Shimizu H., Miyazaki S., Kataoka T., Hori M., Muraoka O.. J. Chem. Soc., Perkin Trans. 1 1994; 3129
  • 7 Appel T. R., Yehia N. A. M., Baumeister U., Hartung H., Kluge R., Ströhl D., Fanghänel E.. Eur. J. Org. Chem 2003; 47
  • 8 Blair I. A., Mander L. N., Mundill P. H. C.. Aust. J. Chem 1981; 34: 1235
  • 9 Ung G., Soleilhavoup M., Bertrand G.. Angew. Chem. Int. Ed 2013; 52: 758
  • 10 Nevado C., Cárdenas D. J., Echavarren A. M.. Chem.–Eur. J 2003; 9: 2627
  • 11 Genin E., Toullec P. Y., Antoniotti S., Brancour C., Genêt J.-P., Michelet V.. J. Am. Chem. Soc 2006; 128: 3112
  • 12 Ritter S., Horino Y., Lex J., Schmalz H.-G.. Synlett 2006; 3309
  • 13 Hashmi A. S. K., Schuster A. M., Gaillard S., Cavallo L., Poater A., Nolan S. P.. Organometallics 2011; 30: 6328
  • 14 Barabé F., Levesque P., Korobkov I., Barriault L.. Org. Lett 2011; 13: 5580
  • 15 Gagosz F.. Synthesis 2019; 51: 1087
  • 16 Jans A. C. H., Caumes X., Reek J. N. H.. ChemCatChem 2019; 11: 287
  • 17 Pan F., Shu C., Ye L.-W.. Org. Biomol. Chem 2016; 14: 9456
  • 18 Day D. P., Chan P. W. H.. Adv. Synth. Catal 2016; 358: 1368
  • 19 Ranieri B., Escofet I., Echavarren A. M.. Org. Biomol. Chem 2015; 13: 7103
  • 20 Dorel R., Echavarren A. M.. Chem. Rev 2015; 115: 9028
  • 21 Goodwin J. A., Aponick A.. Chem. Commun. (Cambridge) 2015; 51: 8730
  • 22 Butkevich A. N., Sednev M. V., Shojaei H., Belov V. N., Hell S. W.. Org. Lett 2018; 20: 1261
  • 23 Sednev M., Butkevich A., Shojaei H., Belov V., Hell S. W., Wurm C., Kamin D.. EP 3 357 928, 2018
  • 24 Clunas S., Strory J. M. D., Rickard J. E., Horsley D., Harrington C. R., Wischik C. M.. WO 2010 067 078, 2010
  • 25 Nealey R. H., Driscoll J. S.. J. Heterocycl. Chem 1966; 3: 228
  • 26 Dilthey W., Quint F., Heinen J.. J. Prakt. Chem 1939; 152: 49
  • 27 Dilthey W., Quint F., Stephan H.. J. Prakt. Chem 1939; 152: 99
  • 28 Wu D., Pisula W., Haberecht M. C., Feng X., Müllen K.. Org. Lett 2009; 11: 5686
  • 29 Tanaka K., Kishimoto M., Sukekawa M., Hoshino Y., Honda K.. Tetrahedron Lett 2018; 59: 3361
  • 30 Tanaka K., Omata D., Asada Y., Hoshino Y., Honda K.. J. Org. Chem 2019; 84: 10 669
  • 31 Srivastava V., Singh P. P.. RSC Adv 2017; 7: 31 377
  • 32 Hari D. P., König B.. Chem. Commun. (Cambridge) 2014; 50: 6688
  • 33 Reiser O.. Acc. Chem. Res 2016; 49: 1990
  • 34 Weiser M., Hermann S., Penner A., Wagenknecht H.-A.. Beilstein J. Org. Chem 2015; 11: 568
  • 35 Yamaguchi T., Yamamoto Y., Fujiwara Y., Tanimoto Y.. Org. Lett 2005; 7: 2739
  • 36 Yamaguchi T., Yamamoto Y., Kinoshita D., Akiba K.-y., Zhang Y., Reed C. A., Hashizume D., Iwasaki F.. J. Am. Chem. Soc 2008; 130: 6894
  • 37 Poleschner H., Seppelt K.. J. Fluorine Chem 2003; 120: 49
  • 38 Zhu X.-Q., Dai Z., Yu A., Wu S., Cheng J.-P.. J. Phys. Chem. B 2008; 112: 11 694
  • 39 Piscopo C. G., Bühler S., Sartori G., Maggi R.. Catal. Sci. Technol 2012; 2: 2449
  • 40 Shen G.-B., Xia K., Li X.-T., Li J.-L., Fu Y.-H., Yuan L., Zhu X.-Q.. J. Phys. Chem. A 2016; 120: 1779
  • 41 Zhu X.-Q., Li X.-T., Han S.-H., Mei L.-R.. J. Org. Chem 2012; 77: 4774
  • 42 Sabatini R. P., Mark M. F., Mark D. J., Kryman M. W., Hill J. E., Brennessel W. W., Detty M. R., Eisenberg R., McCamant D. W.. Photochem. Photobiol. Sci 2016; 15: 1417
  • 43 Del Valle D. J., Donnelly D. J., Holt J. J., Detty M. R.. Organometallics 2005; 24: 3807
  • 44 Erabi T., Asahara M., Miyamoto M., Goto K., Wada M.. Bull. Chem. Soc. Jpn 2002; 75: 1325
  • 45 Barton B., de Jager L., Hosten E. C.. Supramol. Chem 2018; 30: 61
  • 46 Barton B., Jooste D. V., Hosten E. C.. J. Inclusion Phenom. Macrocyclic Chem 2019; 93: 333
  • 47 Olson J. E., Tripp A., Linder M. K., Hu Z., Detty M. R., Jensen L., Camden J. P.. J. Phys. Chem. C 2018; 122: 25 051
  • 48 Tombline G., Donnelly D. J., Holt J. J., You Y., Ye M., Gannon M. K., Nygren C. L., Detty M. R.. Biochemistry 2006; 45: 8034
  • 49 Clark J. L., Hill J. E., Rettig I. D., Beres J. J., Ziniuk R., Ohulchanskyy T. Y., McCormick T. M., Detty M. R.. Organometallics 2019; 38: 2431
  • 50 Gannon II M. K., Holt J. J., Bennett S. M., Wetzel B. R., Loo T. W., Bartlett M. C., Clarke D. M., Sawada G. A., Higgins J. W., Tombline G., Raub T. J., Detty M. R.. J. Med. Chem 2009; 52: 3328
  • 51 Kryman M. W., McCormick T. M., Detty M. R.. Organometallics 2016; 35: 1944
  • 52 Davies K. S., Linder M. K., Kryman M. W., Detty M. R.. Bioorg. Med. Chem 2016; 24: 3908
  • 53 Holt J. J., Gannon II M. K., Tombline G., McCarty T. A., Page P. M., Bright F. V., Detty M. R.. Bioorg. Med. Chem 2006; 14: 8635
  • 54 Kryman M. W., Schamerhorn G. A., Hill J. E., Calitree B. D., Davies K. S., Linder M. K., Ohulchanskyy T. Y., Detty M. R.. Organometallics 2014; 33: 2628
  • 55 Hogan D. T., Sutherland T. C.. J. Phys. Chem. Lett 2018; 9: 2825
  • 56 Katritzky A. R., Ramer W. H.. J. Org. Chem 1985; 50: 852
  • 57 Nagahora N., Kushida T., Shioji K., Okuma K.. Organometallics 2019; 38: 1800
  • 58 Freund T., Scherf U., Müllen K.. Angew. Chem. Int. Ed. Engl 1995; 33: 2424
  • 59 Ahn Y.-H., Lee J.-S., Chang Y.-T.. J. Am. Chem. Soc 2007; 129: 4510
  • 60 Chang Y.-T., Ahn Y.-H.. US 2008 124 751, 2008
  • 61 Detty M. R., Prasad P. N., Donnelly D. J., Ohulchanskyy T., Gibson S. L., Hilf R.. Bioorg. Med. Chem 2004; 12: 2537
  • 62 Gibson S. L., Holt J. J., Ye M., Donnelly D. J., Ohulchanskyy T. Y., You Y., Detty M. R.. Bioorg. Med. Chem 2005; 13: 6394
  • 63 Gibson S. L., Hilf R., Donnelly D. J., Detty M. R.. Bioorg. Med. Chem 2004; 12: 4625
  • 64 Wagner S. J., Skripchenko A., Donnelly D. J., Ramaswamy K., Detty M. R.. Bioorg. Med. Chem 2005; 13: 5927
  • 65 Calitree B., Donnelly D. J., Holt J. J., Gannon M. K., Nygren C. L., Sukumaran D. K., Autschbach J., Detty M. R.. Organometallics 2007; 26: 6248
  • 66 Gannon II M. K., Detty M. R.. J. Org. Chem 2007; 72: 2647
  • 67 Orchard A., Schamerhorn G. A., Calitree B. D., Sawada G. A., Loo T. W., Bartlett M. C., Clarke D. M., Detty M. R.. Bioorg. Med. Chem 2012; 20: 4290
  • 68 Sabatini R. P., Eckenhoff W. T., Orchard A., Liwosz K. R., Detty M. R., Watson D. F., McCamant D. W., Eisenberg R.. J. Am. Chem. Soc 2014; 136: 7740
  • 69 Hagel M., Liu J., Muth O., Rivera H. J. E., Schwake E., Sripanom L., Henkel G., Dyker G.. Eur. J. Org. Chem 2007; 3573
  • 70 Nicolas C., Bernardinelli G., Lacour J.. J. Phys. Org. Chem 2010; 23: 1049
  • 71 Nishida J.-i., Miyagawa T., Yamashita Y.. Org. Lett 2004; 6: 2523
  • 72 Wu L., Burgess K.. Org. Lett 2008; 10: 1779
  • 73 Calitree B. D., Detty M. R.. Synlett 2010; 89
  • 74 Washburn R. M., Levens E., Albright C. F., Billig F. A.. Org. Synth., Coll. Vol. IV 1963; 68
  • 75 Wu X., Liu X., Zhao G.. Tetrahedron: Asymmetry 2005; 16: 2299
  • 76 Ohta E., Nehira T., Kawai H., Fujiwara K., Suzuki T.. Tetrahedron Lett 2008; 49: 777
  • 77 Yamaguchi T., Fuku-en S.-i., Sugawara S., Kojima S., Yamamoto Y.. Aust. J. Chem 2010; 63: 1638
  • 78 Logtenberg H., Areephong J., Bauer J., Meetsma A., Feringa B. L., Browne W. R.. ChemPhysChem 2016; 17: 1895
  • 79 Dong S., Herng T. S., Gopalakrishna T. Y., Phan H., Lim Z. L., Hu P., Webster R. D., Ding J., Chi C.. Angew. Chem. Int. Ed 2016; 55: 9316
  • 80 Chen Y., Kueh H., Gopalakrishna T. Y., Dong S., Han Y., Chi C.. Org. Lett 2019; 21: 3127
  • 81 Berényi S., Tóth M., Gyulai S., Szilágyi L.. Heterocycles 2002; 57: 135
  • 82 Brooks D. W., Lu L. D.-L., Masamune S.. Angew. Chem. Int. Ed. Engl 1979; 18: 72