Synthesis 2015; 47(17): 2663-2669
DOI: 10.1055/s-0034-1380745
paper
© Georg Thieme Verlag Stuttgart · New York

The First Preparation of Azulenylzinc Reagents and Their Use in Negishi Cross-Coupling

Julia Dubovik
Institute of Technology, University of Tartu, Nooruse 1, 50411, Tartu, Estonia   Email: aleksei.bredihhin@ut.ee
,
Aleksei Bredihhin*
Institute of Technology, University of Tartu, Nooruse 1, 50411, Tartu, Estonia   Email: aleksei.bredihhin@ut.ee
› Author Affiliations
Further Information

Publication History

Received: 17 February 2015

Accepted after revision: 16 April 2015

Publication Date:
28 May 2015 (online)


Abstract

The preparation of azulenylzinc reagents from the corresponding iodoazulenes is described. The synthetic utility of the obtained reagents is demonstrated by introducing functionalized aryl and sensitive heterocyclic substituents into the azulene moiety through Negishi cross-coupling.

Supporting Information

 
  • References

    • 1a Kurotobi K, Kim KS, Noh SB, Kim D, Osuka A. Angew. Chem. Int. Ed. 2006; 45: 3944
    • 1b Puodziukynaite E, Wang H.-W, Lawrence J, Wise AJ, Russell TP, Barnes MD, Emrick T. J. Am. Chem. Soc. 2014; 136: 11043
    • 1c Muranaka A, Yonehara M, Uchiyama M. J. Am. Chem. Soc. 2010; 132: 7844
    • 1d Oda M, Thanh NC, Ikai M, Fujikawa H, Nakajima K, Kuroda S. Tetrahedron 2007; 63: 10608
    • 1e Thanh NC, Ikai M, Kajioka T, Fujikawa H, Taga Y, Zhang Y, Ogawa S, Shimada H, Miyahara Y, Kuroda S, Oda M. Tetrahedron 2006; 62: 11227
    • 1f Koch M, Blacque O, Venkatesan K. Org. Lett. 2012; 14: 1580
    • 1g Koch M, Blacque O, Venkatesan K. J. Mater. Chem. C 2013; 1: 7400
  • 2 Ito S, Morita N. Eur. J. Org. Chem. 2009; 4567
    • 3a Yamaguchi Y, Ogawa K, Nakayama K.-I, Ohba Y, Katagiri H. J. Am. Chem. Soc. 2013; 135: 19095
    • 3b Wang F, Lai Y.-H, Kocherginsky NM, Kosteski YY. Org. Lett. 2003; 5: 995
    • 4a Lacroix PG, Malfant I, Iftime G, Razus AC, Nakatani K, Delaire JA. Chem. Eur. J. 2000; 6: 2599
    • 4b Cristian L, Sasaki I, Lacroix PG, Donnadieu B, Asselberghs I, Clays K, Razus AC. Chem. Mater. 2004; 16: 3543
    • 5a Ramadan M, Goeters S, Watzer B, Krause E, Lohmann K, Bauer R, Hempel B, Imming P. J. Nat. Prod. 2006; 69: 1041
    • 5b Rekka E, Chrysselis M, Siskou I, Kourounakis A. Chem. Pharm. Bull. 2002; 50: 904
    • 6a Zhang L-Y, Yang F, Shi W.-Q, Zhang P, Li Y, Yin S.-F. Bioorg. Med. Chem. Lett. 2011; 21: 5722
    • 6b Yanagisawa T, Kosakai K, Tomiyama T, Yasunami M, Takase K. Chem. Pharm. Bull. 1990; 38: 3355
    • 6c Yanagisawa T, Wakabayashi S, Tomiyama T, Yasunami M, Takase K. Chem. Pharm. Bull. 1988; 36: 641
    • 7a Sekine T, Takahashi J, Nishishiro M, Arai A, Wakabayashi H, Kurihara T, Kobayashi M, Hashimoto K, Kikuchi H, Katayama T, Kanda Y, Kunii S, Motohashi N, Sakagami H. Anticancer Res. 2007; 27: 133
    • 7b Wakabayashi H, Hashiba K, Yokoyama K, Hashimoto K, Kikuchi H, Nishikawa H, Kurihara T, Satoh K, Shioda S, Sato S, Kusano S, Nakashima H, Motohashi N, Sakagami H. Anticancer Res. 2003; 23: 4747
    • 7c Asato AE, Peng A, Hossain MZ, Mirzadegan T, Bertram JS. J. Med. Chem. 1993; 36: 3137
    • 7d Ishihara M, Wakabayashi H, Motohashi N, Sakagami H. Anticancer Res. 2011; 31: 515
  • 8 Kurotobi K, Tabata H, Miyauchi M, Rahman AF. M. M, Migita K, Murafuji T, Sugihara Y, Shimoyama H, Fujimori K. Synthesis 2003; 30
  • 9 McDonald RN, Petty HE, Wolfe NL, PaukstelisJ V. J. Org. Chem. 1974; 39: 1877
  • 10 Morita T, Abe N, Takase K. J. Chem. Soc., Perkin Trans. 1 2000; 3063
  • 11 Shibasaki T, Ooishi T, Yamanouchi N, Murafuji T, Kurotobi K, Sugihara Y. J. Org. Chem. 2008; 73: 7971
  • 12 Ito S, Kubo T, Morita N, Matsui Y, Watanabe T, Ohta A, Fujimori K, Murafuji T, Sugihara Y, Tajiri A. Tetrahedron Lett. 2004; 45: 2891
  • 13 Ito S, Terazono T, Kubo T, Okujima T, Morita N, Murafuji T, Sugihara Y, Fujimori K, Kawakami J, Tajiri A. Tetrahedron 2004; 60: 5357
  • 14 Ito S, Shoji T, Morita N. Synlett 2011; 2279
  • 15 Fujinaga M, Suetake K, Gyoji K, Murafuji T, Kurotobi K, Sugihara Y. Synthesis 2008; 3745
  • 16 Ito S, Okujima T, Morita N. J. Chem. Soc., Perkin Trans. 1 2002; 1896
  • 17 Okujima T, Ito S, Morita N. Tetrahedron Lett. 2002; 43: 1261
  • 18 Kurotobi K, Miyauchi M, Takakura K, Murafuji T, Sugihara Y. Eur. J. Org. Chem. 2003; 3663
  • 19 Rahman AF. M. M, Murafuji T, Kurotobi K, Sugihara Y. Organometallics 2004; 23: 6176
    • 20a Crombie AL, Kane JL, Shea KM, Danheiser RL. J. Org. Chem. 2004; 69: 8652
    • 20b Ito S, Ueda M, Sekiguchi R, Kawakami J. Tetrahedron 2013; 69: 4259
  • 21 Dubovik J, Bredihhin A. Synthesis 2015; 47: 538
    • 22a Koch M, Blacque O, Venkatesan K. Org. Lett. 2012; 14: 1580
    • 22b Ito S, Nomura A, Morita N, Kabuto C, Kobayashi H, Maejima S, Fujimori K, Yasunami M. J. Org. Chem. 2002; 67: 7295
  • 23 Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
  • 24 Iwama S. JP2004035519 A, 2004 ; Chem. Abstr. 2004, 140, 163698.
  • 25 Shoji T, Ito S, Toyota K, Iwamoto T, Yasunami M, Morita N. Eur. J. Org. Chem. 2009; 4307
  • 26 Shoji T, Kikuchi S, Ito S, Morita N. Heterocycles 2005; 66: 91