Synlett 2020; 31(09): 903-906
DOI: 10.1055/s-0039-1690850
letter
© Georg Thieme Verlag Stuttgart · New York

Ligand-Free and Solvent-Free Synthesis of 1,3-Disubstituted Naphthalenes through Stille Coupling

Sanae Sbi
a  Laboratory of Analytical and Molecular Chemistry, Department of Chemistry, University Cadi Ayyad, Faculty Polydisciplinaire of Safi, Sidi Bouzid 46000 Safi, Morocco   Email: [email protected]
,
Victor Mkpenie
b  Department of Chemistry, University of Uyo, P. M. B. 1017, Uyo, Nigeria
,
Kiyoshi Tanemura
c  Chemical Laboratory, School of Life Dentistry at Niigata, Nippon Dental University, Hamaura-cho, Niigata 951-8580, Japan
,
a  Laboratory of Analytical and Molecular Chemistry, Department of Chemistry, University Cadi Ayyad, Faculty Polydisciplinaire of Safi, Sidi Bouzid 46000 Safi, Morocco   Email: [email protected]
› Author Affiliations
T.R. is grateful to the University Cadi Ayyad, especially the Faculty Polydisciplinaire of Safi, for the financial support given to the Laboratory of Analytical and Molecular Chemistry. K.T. thanks Nippon Dental University for the financial support to the Chemical Laboratory.
Further Information

Publication History

Received: 14 January 2020

Accepted after revision: 18 February 2020

Publication Date:
20 March 2020 (online)


Abstract

A variety of 1,3-disubstituted naphthalenes have been prepared by palladium-catalyzed annulation of (o-ethynylphenyl)acetyl chloride with design of a new synthetic strategy by Stille coupling using functionalized organostannanes. The method affords excellent yields of the substituted naphthalenes and accommodates a wide variety of functional groups under mild conditions. Mechanistic studies show intramolecular cyclization as a major step following C–C bond coupling.

Supporting Information

 
  • References and Notes

  • 1 Edelmann FT. Coord. Chem. Rev. 2017; 338: 27
  • 2 Cao J, London G, Dumele O, Rekowski VW. M, Trapp N, Ruhlmann L, Boudon C, Stanger A, Diederich F. J. Am. Chem. Soc. 2015; 137: 7178
  • 3 Roncali J, Leriche P, Blanchard P. Adv. Mater. 2014; 26: 3821
  • 4 Stockdale TP, Williams CM. Chem. Soc. Rev. 2015; 44: 7737
  • 5 Vij V, Bhalla V, Kumar M. Chem. Rev. 2016; 116: 9565
  • 6 Zhang L, Cao Y, Colella NS, Liang Y, Brédas JL, Houk KN, Briseno AL. Acc. Chem. Res. 2015; 48: 500
  • 7 Ingale SA. Seela F. 2012; 77: 9352
  • 8 Li Q, Peng M, Li H, Zhong C, Zhang L, Cheng X, Peng X, Wang Q, Qin J, Li Z. Org. Lett. 2012; 14: 2094
  • 9 Wang Z, Xu H. Tetrahedron Lett. 2019; 60: 664
  • 10 Colby DA, Tsai AS, Bergman PG, Ellman JA. Acc. Chem. Res. 2012; 45: 814
  • 11 Huang Z, Lim HN, Mo F, Young MC, Dong G. Chem. Soc. Rev. 2015; 44: 7764
  • 12 Zhao X, Zhang XG, Tang RY, Deng CL, Li JH. Eur. J. Org. Chem. 2010; 4211
  • 13 Tan X, Liu BX, Li XY, Li B, Xu SS, Song HB, Wang BQ. J. Am. Chem. Soc. 2012; 134: 16163
  • 14 Zhou S, Wang J, Wang L, Song C, Chen K, Zhu J. Angew. Chem. Int. Ed. 2016; 55: 9384
  • 15 Adak L, Yoshikai N. Tetrahedron 2012; 68: 5167
  • 16 Umeda R, Nishi S, Kojima A, Kaiba K, Nishiyama Y. Tetrahedron Lett. 2013; 54: 179
  • 17 Asao N. Synlett 2006; 1645
  • 18 Asao N, Nogami T, Lee S, Yamamoto Y. J. Am. Chem. Soc. 2003; 125: 10921
  • 19 Sun H, Wu X, Hua R. Tetrahedron Lett. 2011; 52: 4408
  • 20 Cho CS, Lim DK, Zhang JQ, Kim T, Shim SC. Tetrahedron Lett. 2004; 45: 5653
  • 21 Hein SJ, Lehnherr D, Arslan H, Uribe-Romo FJ, Dichtel WR. Acc. Chem. Res. 2017; 50: 2776
  • 22 Asao N, Nogami T, Lee S, Yamamoto Y. J. Am. Chem. Soc. 2003; 125: 10921
  • 23 Huang Q, Larock RC. Org. Lett. 2002; 4: 2505
  • 24 Larock RC, Yum EK, Refvik MD. J. Org. Chem. 1998; 63: 7652
  • 25 Roesch KR, Zhang H, Larock RC. J. Org. Chem. 2001; 66: 8042
  • 26 Larock RC, Yum EK, Doty MJ, Sham KK. C. J. Org. Chem. 1995; 60: 3270
  • 27 Larock RC, Tian Q. J. Org. Chem. 1998; 63: 2002
  • 28 Kim JN, Im YJ, Gong JH, Lee KY. Tetrahedron Lett. 2001; 42: 4195
  • 29 Smith AL, Nicolaou KC. J. Med. Chem. 1996; 39: 2103
  • 30 Kobayashi S, Reddy RS, Sugiura Y, Sasaki D, Miyagawa N, Hirama M. J. Am. Chem. Soc. 2001; 123: 2887
  • 31 Lipshutz BH, Keith J. Angew. Chem. Int. Ed. 1999; 38: 3530
  • 32 One-Pot Synthesis of Naphthalenes 3–22; General Procedure A Schlenk reaction tube was successively charged with alkyne 1 (0.2 mmol), R1SnBu3 (0.4 mmol), R2SnBu3 (0.4 mmol), and Pd(PPh3)4 (5 mol%, 0.01 mmol). The reaction mixture was stirred and heated at 60 °C for 8 h. The reaction was monitored by TLC and the absence of any trace of the starting material indicated completion of the reaction. The reaction mixture was washed with sat. aq NaHCO3 solution (2×10 mL) and distilled water (10 mL), and then poured into ethyl acetate. The aqueous layer was extracted with ethyl acetate and the organic layer was then dried with Mg2SO4 (anhydrous). The solvent was evaporated under vacuum. Product 3 was obtained by flash column chromatography (heptane/ethyl acetate). Identification of 3 was carried out by comparison with the data reported in the literature33 (see Supporting Information).
  • 33 Jagdale AR, Park JH, Youn SW. J. Org. Chem. 2011; 76: 7204