Synthesis 2013; 45(17): 2469-2473
DOI: 10.1055/s-0033-1338500
paper
© Georg Thieme Verlag Stuttgart · New York

Phenylated Benzotetraphenes (Dibenzanthracenes) by Nickel-Catalyzed Diphenylacetylene Cycloadditions to Linear [3]Phenylenes

Zhenhua Gu
Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA   Fax: +1(510)6435208   eMail: kpcv@berkeley.edu
,
K. Peter C. Vollhardt*
Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA   Fax: +1(510)6435208   eMail: kpcv@berkeley.edu
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Publikationsverlauf

Received: 01. Mai 2013

Accepted after revision: 04. Juni 2013

Publikationsdatum:
24. Juni 2013 (online)


Abstract

Ni(COD)(PMe3)2 catalyzes the cycloaddition of diphenylacetylene to the four-membered rings of linear [3]phenylene and its 2,3,7,8-tetrakis(trimethylsilyl) derivative. The reaction proceeds via initial formation of the 5,6-diphenylbenzo[3,4]cyclobuta[1,2-b]phenanthrene frame, followed by a competitive second, nonregio­selective alkyne insertion to furnish the corresponding phenyl-­substituted benzo[k]- and -[m]tetraphenes.

Supporting Information

 
  • References


    • For very recent reviews, see:
    • 1a Li J, Zhang Q. Synlett 2013; 24: 686
    • 1b Gingras M. Chem. Soc. Rev. 2013; 42: 968
    • 1c Gingras M. Chem. Soc. Rev. 2013; 42: 1007
    • 1d Sun Z, Ye Q, Chi C, Wu J. Chem. Soc. Rev. 2012; 41: 7857
    • 1e Zhang H, Wu D, Liu SH, Yin J. Curr. Org. Chem. 2012; 16: 2124
    • 1f Sun Z, Wu J. J. Mater. Chem. 2012; 22: 4151

    • For very recent illustrative methodologies, see:
    • 1g Ilies L, Matsumoto A, Kobayashi M, Yoshikai N, Nakamura E. Synlett 2012; 23: 2381
    • 1h Zhou J, Yang W, Wang B, Ren H. Angew. Chem. Int. Ed. 2012; 51: 12293
    • 1i Arslan H, Saathoff JD, Bunck DN, Clancy P, Dichtel WR. Angew. Chem. Int. Ed. 2012; 51: 12051
    • 1j Xia Y, Liu Z, Xiao Q, Qu P, Ge R, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2012; 51: 5714
    • 1k Li Y, Heng W.-K, Lee BS, Aratani N, Zafra JL, Bao N, Lee R, Sung YM, Sun Z, Huang K.-W, Webster RD, López Navarrete JT, Kim D, Osuka A, Casado J, Ding J, Wu J. J. Am. Chem. Soc. 2012; 134: 14913
    • 1l Zeng Z, Sung YM, Bao N, Tan D, Lee R, Zafra JL, Lee BS, Ishida M, Ding J, López Navarrete JT, Li Y, Zeng W, Kim D, Huang K.-W, Webster RD, Casado J, Wu J. J. Am. Chem. Soc. 2012; 134: 14513
    • 1m Kumar B, Strasser CE, King BT. J. Org. Chem. 2012; 77: 311
    • 1n Gu X, Luhman WA, Yagodkin E, Holmes RJ, Douglas CJ. Org. Lett. 2012; 14: 1390
    • 1o Umeda R, Miyake S, Nishiyama Y. Chem. Lett. 2012; 41: 215
    • 1p Wu T.-C, Wu Y.-T. Synlett 2011; 741

      For a very recent monograph and reviews, see:
    • 2a Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions, and Coordination Chemistry. Scott LT, Petrukhina MA. Wiley; Hoboken: 2012
    • 2b Ivanovskii AL. Russ. Chem. Rev. 2012; 81: 571
    • 2c Itami K. Pure Appl. Chem. 2012; 84: 907
    • 2d Wen B, Wang KK. Pure Appl. Chem. 2012; 84: 893
    • 2e Sygula A. Eur. J. Org. Chem. 2011; 1611

    • For very recent illustrative methodologies, see:
    • 2f Luo J, Xu X, Mao R, Miao Q. J. Am. Chem. Soc. 2012; 134: 13796
    • 2g Nishiuchi T, Feng X, Enkelmann V, Wagner M, Müllen K. Chem. Eur. J. 2012; 18: 16621
    • 2h Fort EH, Jeffreys MS, Scott LT. Chem. Commun. 2012; 48: 8102
    • 2i Li H, He K.-H, Liu J, Wang B.-Q, Zhao K.-Q, Hu P, Shi Z.-J. Chem. Commun. 2012; 48: 7028
    • 2j Yamaguchi R, Hiroto S, Shinokubo H. Org. Lett. 2012; 14: 2472
    • 2k Wan X, Chen K, Liu D, Chen J, Miao Q, Xu J. Chem. Mater. 2012; 24: 3906
    • 2l Higashibayashi S, Tsuruoka R, Soujanya Y, Purushotham U, Sastry GN, Seki S, Ishikawa T, Toyota S, Sakurai H. Bull. Chem. Soc. Jpn. 2012; 85: 450
    • 2m Mueller A, Amsharov KYu. Eur. J. Org. Chem. 2012; 6155
  • 3 For a recent illustrative study, see: De Rouville H.-PJ, Garbage R, Cook RE, Pujol AR, Sirven AM, Rapenne G. Chem. Eur. J. 2012; 18: 3023

    • For recent pertinent investigations, see:
    • 4a Chang M.-Y, Wu M.-H. Tetrahedron 2013; 69: 129
    • 4b Wu A, Xu D, Lu D, Penning TM, Blair IA, Harvey RG. Tetrahedron 2012; 68: 7217
    • 4c Samanta K, Kar GK, Sarkar AK. Polycyclic Aromat. Compd. 2012; 32: 515

      For recent topical disclosures, see:
    • 5a Shimizu M, Tomioka Y, Nagao I, Kadowaki T, Hiyama T. Chem. Asian J. 2012; 7: 1644
    • 5b Lin Y.-D, Cho C.-L, Ko C.-W, Pulte A, Wu Y.-T. J. Org. Chem. 2012; 77: 9979
    • 6a Harvey RG. Polycyclic Aromatic Hydrocarbons . Wiley-VCH; New York: 1997
    • 6b Harvey RG. Curr. Org. Chem. 2004; 8: 303
  • 7 Gu Z, Boursalian GB, Gandon V, Padilla R, Shen H, Timofeeva TV, Tongwa P, Vollhardt KP. C, Yakovenko AA. Angew. Chem. Int. Ed. 2011; 50: 9413
  • 8 For a subsequent complementary study employing Ir and Rh catalysts in cycloadditions to 2,3,8,9-tetrakis(trimethylsilyl) angular [3]phenylene, see: Korotvička A, Císařová I, Roithová J, Kotora M. Chem. Eur. J. 2012; 18: 4200
    • 9a For a review of the parent phenylenes, see: Miljanić OŠ, Vollhardt KP. C. In Carbon-Rich Compounds: From Molecules to Materials . Haley MM, Tykwinski RR. Wiley-VCH; Weinheim: 2006: 140 ; and references cited therein

    • For subsequent work, see:
    • 9b Mohler DL, Kumaraswamy S, Stanger A, Vollhardt KP. C. Synlett 2006; 2981
    • 9c Dosche C, Mickler W, Löhmannsröben H.-G, Agenet N, Vollhardt KP. C. J. Photochem. Photobiol., A 2007; 188: 371
    • 9d Agenet N, Gandon V, Vollhardt KP. C, Malacria M, Aubert C. J. Am. Chem. Soc. 2007; 129: 8860
    • 9e Eichberg MJ, Houk KN, Lehmann J, Leonard PW, Märker A, Norton JE, Sawicka D, Vollhardt KP. C, Whitener GD, Wolff S. Angew. Chem. Int. Ed. 2007; 46: 6894
    • 9f Dosa PI, Gu Z, Hager D, Karney WL, Vollhardt KP. C. Chem. Commun. 2009; 1967
    • 9g Engelhardt V, Garcia JG, Hubaud AA, Lyssenko KA, Spyroudis S, Timofeeva TV, Tongwa P, Vollhardt KP. C. Synlett 2011; 280
    • 9h González Gómez JA, Green J, Vollhardt KP. C. Synlett 2011; 805
    • 9i Balaban AT, Vollhardt KP. C. Open Org. Chem. J. 2011; 5 (Suppl. 01) 117
    • 9j Albright TA, Oldenhoff S, Oloba OA, Padilla R, Vollhardt KP. C. Chem. Commun. 2011; 47: 9039
  • 10 Buckland PR, Hacker NP, McOmie JF. W. J. Chem. Soc., Perkin Trans. 1 1983; 1443
  • 11 Balaban AT, Gutman I, Marković S, Simijonović D, Ðurđević J. Polycyclic Aromat. Compd. 2011; 31: 339
  • 12 The structures of the benzologous benzocyclobuta[b] [4]-, [5]-, and [6]helicene have been determined: Van Meerssche PM, Germain G, Declercq JP, Soubrier-Payen B, Figeys HP, Vanommeslaeghe P. Acta Crystallogr., Sect. B 1981; 37: 1218
  • 13 CCDC 936535 contains the supplementary crystallographic data for 8b. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • 14a See, for example, a comparison of X-ray data for 7a with 7b: Schleifenbaum A, Feeder N, Vollhardt KP. C. Tetrahedron Lett. 2001; 42: 7329
    • 14b Similarly, compare the structure of 5,6,7,8-tetraphenyl[5]phenacene (ref. 7) with that of its 2,3,10,11-tetrakis(trimethylsilyl) derivative (ref. 8).
  • 15 Schaub T, Backes M, Radius U. Organometallics 2006; 25: 4196
  • 16 Gutman I, Ashrafi AR. MATCH 2008; 60: 135
  • 17 Mayneord WV, Roe EM. F. Proc. R. Soc. London, Ser. A 1935; 152: 299

    • See, for example:
    • 18a Parkhurst RR, Swager TM. J. Am. Chem. Soc. 2012; 134: 15351
    • 18b Nakatsuka M. JP 2010219301, 2010
    • 18c Watanabe M, Ohashi T. JP 2010070473, 2010
    • 18d Watanabe M, Ohashi T. JP 2010070473, 2010
    • 18e Katakura R, Ozeki H, Okubo Y. JP 2007208032, 2007
    • 18f Taillemite S, Aubert C, Fichou D, Malacria M. Tetrahedron Lett. 2005; 46: 8325
    • 19a Spectral Atlas of Polycyclic Aromatic Compounds . Karcher W, Fordham RJ, Dubois JJ, Glaude PG. J. M, Ligthart JA. M. D. Reidel; Dordrecht: 1985
    • 19b Zertani R, Meier H. Chem. Ber. 1986; 119: 1704
    • 19c Ozubko RS, Buchanan GW, Smith IC. P. Can. J. Chem. 1974; 52: 2493
  • 20 Hseuh H.-H, Hsu M.-Y, Wu T.-L, Liu R.-S. J. Org. Chem. 2009; 74: 8448
    • 21a Je JT, Jung SU, Park JH, Yoo YG. KR 2012117694, 2012
    • 21b Park JH, Mun SY, Baek JY, Choi DH, Kim DH, Hong CK. KR 20100111037, 2010

      For recent work, see:
    • 22a Toyoshima T, Yoshida S, Watanabe S. Tetrahedron 2013; 69: 1904
    • 22b Nakae T, Ohnishi R, Kitahata Y, Soukawa T, Sato H, Mori S, Okujima T, Uno H, Sakaguchi H. Tetrahedron Lett. 2012; 53: 1617
    • 22c Kitazawa K, Kochi T, Nitani M, Ie Y, Aso Y, Kakiuchi F. Chem. Lett. 2011; 40: 300