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

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.

Key words

ethynylbenzene - organostannanes - 1,3-disubstituted naphthalenes - Stille coupling - palladium(0) catalysis

• 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