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Christmann, M. et al.: 2020 Science of Synthesis: Knowledge Updates 2020/2 DOI: 10.1055/sos-SD-105-00210
Knowledge Updates 2020/2

5.1.28 Product Subclass 28: Germoles

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Buch

Herausgeber: Christmann, M.; Huang, Z.; Joule, J. A.; Li, C.-J.; Li, J.; Marschner, C.; Petersson, E. J.; Reißig, H.-U.; Schaumann, E.; Terent'ev, A. 

Autoren: Ambhaikar, N.; Campagne, J.-M.; Celik, I.; Dembitsky, V.; Graham, M.; Holzschneider, K.; Jaschinski, M.; Kipke, W.; Kirsch, S.; Kunz, K.; Leclerc, E.; Li, G.; Li, Z.; Makow, J.; Müller, T.; Ochoa, C. I.; Ramirez y Medina, I.-M. .; Rayner, C. M.; Staubitz, A.; Sun, X.-L.; Szostak, M.; Tambar, U. K.; Tian, T.; Tong, M.; Wang, X.-Y.; Yaremenko, I.; Yoshikai, N.

Titel: Knowledge Updates 2020/2

Print ISBN: 9783132435612; Online ISBN: 9783132435636; Buch-DOI: 10.1055/b000000103

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

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Knowledge Updates



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

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

Typ: Mehrbändiges Werk

Auch verfügbar auf
 

Abstract

This chapter provides an overview of methods for the synthesis of 1H-germoles. It covers the literature from 1959 until 2020. Classical methods involve the cyclization of 1,4-dilithiobuta-1,3-dienes and zirconium/germanium exchange in zirconacyclopentadienes, but more-recent approaches such as catalytic double hydrogermylations of butadiynes are included as well. Finally, methods for the preparation of alkali metal salts of 1H-germol-1-ides and 1H-germol-1,1-diides are summarized.

Schlüsselwörter

germoles - anionic reagents - alkynes - butadienes - butadiynes - germanium compounds - germanes - iodo compounds - lithium compounds - zirconocenes
 
  • 1 Khabashesku, V. N., Boganov, S. E., Antic, D., Nefedov, O. M., Michl, J.. Organometallics. 1996; 15: 4714
    Google Scholar
  • 2 Jorner, K., Emanuelsson, R., Dahlstrand, C., Tong, H., Denisova, A. V., Ottosson, H.. Chem.–Eur. J.. 2014; 20: 9295
    Google Scholar
  • 3 Yamaguchi, S., Tamao, K.. Bull. Chem. Soc. Jpn.. 1996; 69: 2327
    Google Scholar
  • 4 Luo, J., Xie, Z., Lam, J. W. Y., Cheng, L., Chen, H., Qiu, C., Kwok, H. S., Zhan, X., Liu, Y., Zhu, D., Tang, B. Z.. Chem. Commun. (Cambridge). 2001; 1740
    Google Scholar
  • 5 Law, C. C. W., Chen, J., Lam, J. W. Y., Peng, H., Tang, B. Z.. J. Inorg. Organomet. Polym.. 2004; 14: 39
    Google Scholar
  • 6 Adachi, Y., Ohshita, J., Main Group Strategies towards Functional Hybrid Materials. Baumgartner, T., Jäkle, F.. Wiley; Hoboken 2017. 237.
    Google Scholar
  • 7 Saito, M., Yoshioka, M.. Coord. Chem. Rev.. 2005; 249: 765
    Google Scholar
  • 8 Dong, Z., Albers, L., Müller, T.. Acc. Chem. Res.. 2020; 53: 532
    Google Scholar
  • 9 Matsuda, T., Kadowaki, S., Yamaguchi, Y., Murakami, M.. Org. Lett.. 2010; 12: 1056
    Google Scholar
  • 10 Tobisu, M., Baba, K., Chatani, N.. Org. Lett.. 2011; 13: 3282
    Google Scholar
  • 11 Murai, M., Matsumoto, K., Okada, R., Takai, K.. Org. Lett.. 2014; 16: 6492
    Google Scholar
  • 12 Zhou, D., Gao, Y., Liu, B., Tan, Q., Xu, B.. Org. Lett.. 2017; 19: 4628
    Google Scholar
  • 13 Akahori, S., Sakai, H., Hasobe, T., Shinokubo, H., Miyake, Y.. Org. Lett.. 2018; 20: 304
    Google Scholar
  • 14 Leavitt, F. C., Manuel, T. A., Johnson, F.. J. Am. Chem. Soc.. 1959; 81: 3163
    Google Scholar
  • 15 Leavitt, F. C., Manuel, T. A., Johnson, F., Matternas, L. U., Lehman, D. S.. J. Am. Chem. Soc.. 1960; 82: 5099
    Google Scholar
  • 17 West, R., Sohn, H., Powell, D. R., Müller, T., Apeloig, Y.. Angew. Chem. Int. Ed. Engl.. 1996; 35: 1002
    Google Scholar
  • 18 Rausch, M. D., Klemann, L. P., Boon, W. H.. Synth. React. Inorg. Met.-Org. Chem.. 1985; 15: 923
    Google Scholar
  • 19 Barton, T. J., Nelson, A. J., Clardy, J.. J. Org. Chem.. 1972; 37: 895
    Google Scholar
  • 20 Liu, Y., Ballweg, D., Müller, T., Guzei, I. A., Clark, R. W., West, R.. J. Am. Chem. Soc.. 2002; 124: 12 174
    Google Scholar
  • 21 Ohshita, J., Nakamura, M., Ooyama, Y.. Organometallics. 2015; 34: 5609
    Google Scholar
  • 22 Tanikawa, T., Saito, M., Guo, J. D., Nagase, S., Minoura, M.. Eur. J. Org. Chem.. 2012; 7135
    Google Scholar
  • 23 Yasuike, S., Iida, T., Okajima, S., Yamaguchi, K., Seki, H., Kurita, J.. Tetrahedron. 2001; 57: 10 047
    Google Scholar
  • 24 Shynkaruk, O., He, G., McDonald, R., Ferguson, M. J., Rivard, E.. Chem.–Eur. J.. 2016; 22: 248
    Google Scholar
  • 25 Zong, K., Deininger, J. J., Reynolds, J. R.. Org. Lett.. 2013; 15: 1032
    Google Scholar
  • 26 Fei, Z., Ashraf, R. S., Han, Y., Wang, S., Yau, C. P., Tuladhar, P. S., Anthopoulos, T. D., Chabinyc, M. L., Heeney, M.. J. Mater. Chem. A. 2015; 3: 1986
    Google Scholar
  • 27 Zhang, F.-B., Ooyama, Y., Ohshita, J.. ChemistrySelect. 2017; 2: 3106
    Google Scholar
  • 28 Zhang, F.-B., Adachi, Y., Ooyama, Y., Ohshita, J.. Organometallics. 2016; 35: 2327
    Google Scholar
  • 29 Ohshita, J., Murakami, K., Tanaka, D., Ooyama, Y., Mizumo, T., Kobayashi, N., Higashimura, H., Nakanishi, T., Hasegawa, Y.. Organometallics. 2014; 33: 517
    Google Scholar
  • 30 Murakami, K., Ooyama, Y., Higashimura, H., Oshita, J.. Organometallics. 2016; 35: 20
    Google Scholar
  • 31 Yabusaki, Y., Ohshima, N., Kondo, H., Kusamoto, T., Yamanoi, Y., Nishihara, H.. Chem.–Eur. J.. 2010; 16: 5581
    Google Scholar
  • 32 Fagan, P. J., Nugent, W. A., Calabrese, J. C.. J. Am. Chem. Soc.. 1994; 116: 1880
    Google Scholar
  • 33 Fagan, P. J., Nugent, W. A.. J. Am. Chem. Soc.. 1988; 110: 2310
    Google Scholar
  • 34 Lucht, B. L., Buretea, M. A., Tilley, T. D.. Organometallics. 2000; 19: 3469
    Google Scholar
  • 35 Hong, J.-H., Pan, Y., Boudjouk, P.. Angew. Chem. Int. Ed. Engl.. 1996; 35: 186
    Google Scholar
  • 36 Meier-Brocks, F., Weiss, E.. J. Organomet. Chem.. 1993; 453: 33
    Google Scholar
  • 37 Dufour, P., Dartiguenave, M., Dartiguenave, Y., Dubac, J.. J. Organomet. Chem.. 1990; 384: 61
    Google Scholar
  • 38 Freeman, W. P., Tilley, T. D., Liable-Sands, L. M., Rheingold, A. L.. J. Am. Chem. Soc.. 1996; 118: 10 457
    Google Scholar
  • 39 Yamaguchi, S., Itami, Y., Tamao, K.. Organometallics. 1998; 17: 4910
    Google Scholar
  • 40 Westerhausen, M., Stein, B., Ossberger, M. W., Görls, H., Galvez Ruiz, J. C., Nöth, H., Mayer, P.. ARKIVOC. 2007; 46
    Google Scholar
  • 41 Zhou, W.-M., Tomita, I.. Polym. Bull. (Berlin). 2008; 61: 603
    Google Scholar
  • 42 Urrego-Riveros, S., Ramirez y Medina, I.-M., Duvinage, D., Lork, E., Sönnichsen, F. D., Staubitz, A.. Chem.–Eur. J.. 2019; 25: 13 318
    Google Scholar
  • 43 Kanj, A., Meunier, P., Gautheron, B., Dubac, J., Daran, J.-C.. J. Organomet. Chem.. 1993; 454: 51
    Google Scholar
  • 44 Matsuda, T., Transition-Metal-Mediated Aromatic Ring Construction. Tanaka, K.. Wiley; Hoboken 2013. 537.
    Google Scholar
  • 45 Wrackmeyer, B.. J. Organomet. Chem.. 1986; 310: 151
    Google Scholar
  • 46 Köster, R., Seidel, G., Klopp, I., Krüger, C., Kehr, G., Süß, J., Wrackmeyer, B.. Chem. Ber.. 1993; 126: 1385
    Google Scholar
  • 47 Wrackmeyer, B., Bayer, S., Milius, W., Klimkina, E. V.. J. Organomet. Chem.. 2018; 865: 80
    Google Scholar
  • 49 Matsuda, T., Yamaguchi, Y., Murakami, M.. Synlett. 2008; 561
    Google Scholar
  • 50 Tsumuraya, T., Ando, W.. Organometallics. 1990; 9: 869
    Google Scholar
  • 52 Laporterie, A., Manuel, G., Dubac, J., Mazerolles, P., Iloughmane, H.. J. Organomet. Chem.. 1981; 210: C33
    Google Scholar
  • 53 Manuel, G., Mazerolles, P., Lesbre, M., Pradel, J.-P.. J. Organomet. Chem.. 1973; 61: 147
    Google Scholar
  • 54 Manuel, G., Bertrand, G., El Anba, F.. Organometallics. 1983; 2: 391
    Google Scholar
  • 55 Dubac, J., Laporterie, A., Iloughmane, H.. J. Organomet. Chem.. 1985; 293: 295
    Google Scholar
  • 56 Laporterie, A., Iloughmane, H., Dubac, J.. J. Organomet. Chem.. 1983; 244: C12
    Google Scholar
  • 57 Schriewer, M., Neumann, W. P.. J. Am. Chem. Soc.. 1983; 105: 897
    Google Scholar
  • 58 Mochida, K., Akazawa, M., Goto, M., Sekine, A., Ohashi, Y., Nakadaira, Y.. Organometallics. 1998; 17: 1782
    Google Scholar
  • 59 Jutzi, P., Karl, A.. J. Organomet. Chem.. 1981; 215: 19
    Google Scholar
  • 60 Dufour, P., Dubac, J., Dartiguenave, M., Dartiguenave, Y.. Organometallics. 1990; 9: 3001
    Google Scholar
  • 61 Colomer, E., Corriu, R. J. P., Lheureux, M.. Chem. Rev.. 1990; 90: 265
    Google Scholar
  • 62 Freeman, W. P., Tilley, T. D., Arnold, F. P., Rheingold, A. L., Gantzel, P. K.. Angew. Chem. Int. Ed. Engl.. 1995; 34: 1887
    Google Scholar
  • 63 Dong, Z., Schmidtmann, M., Müller, T.. Chem.–Eur. J.. 2019; 25: 10 858
    Google Scholar
  • 64 Choi, S.-B., Boudjouk, P., Hong, J.-H.. Organometallics. 1999; 18: 2919
    Google Scholar
  • 65 Dong, Z., Reinhold, C. R. W., Schmidtmann, M., Müller, T.. Organometallics. 2018; 37: 4736
    Google Scholar
  • 66 Choi, S.-B., Boudjouk, P., Qin, K.. Organometallics. 2000; 19: 1806
    Google Scholar