Synthesis of 2-Acyl-3-arylnaphthalenes by Dual Catalysis of Sodium Tetrachloroaurate toward Alkyne-Propargylic Acetates

Abstract

A new and highly convenient Au-catalyzed cyclization of alkyne-propargylic acetates leading to 2-acyl-3-arylnaphthalene derivatives is described; these are possible candidates for light-emitting materials.

Key words

naphthalene - sodium tetrachloroaurate - gold catalyst - alkyne - cyclization

References and Notes

• For selected reviews, see:
• 1a Trost BM. Krische MJ. Synlett  1998,  1 
• 1b Aubert C. Buisine O. Malacria M. Chem. Rev.  2002,  102:  813 
• 1c Echavarren AM. Nevado C. Chem. Soc. Rev.  2004,  33:  431 
• 2a For reviews of Au-catalyzed reactions, see: Dyker G. Angew. Chem. Int. Ed.  2000,  39:  4237 
• 2b Hashmi ASK. Gold Bull.  2003,  36:  3 
• 2c For selected examples for gold carbene species, see: Luzung MR. Markham JP. Toste FD. J. Am. Chem. Soc.  2004,  126:  10858 
• 2d Zhang L. Kozmin SA. J. Am. Chem. Soc.  2004,  126:  11806 
• 2e Zhang L. Kozmin SA. J. Am. Chem. Soc.  2005,  127:  6963 
• 2f Nieto-Oberhuber C. López S. Echavarren AM. J. Am. Chem. Soc.  2005,  127:  6178 
• 2g Fürstner A. Hannen P. Chem. Commun.  2004,  2546 
• 3a Shin S. Gupta AK. Rhim CY. Oh CH. Chem. Commun.  2005,  4429 
• 3b For recent benzannulation of enynals, see: Kim N. Kim YM. Park W. Sung D. Gupta AK. Oh CH. Org. Lett.  2005,  7:  5289 
• 3c Ohe K. Miki K. Yokoi T. Nishino F. Uemura S. Organometallics  2000,  19:  5525 
• 3d Ohe K. Yokoi T. Miki K. Nishino F. Uemura S. J. Am. Chem. Soc.  2002,  124:  526 
• 4a Myers AG. Harrington PM. Kown BM. J. Am. Chem. Soc.  1992,  114:  1086 
• 4b Sugiyama H. Fujiwara T. Kawabata H. Yoda N. Hirayama N. Saito I. J. Am. Chem. Soc.  1992,  114:  5573 
• 5 Zhao J. Hughes CO. Toste FD. J. Am. Chem. Soc.  2006,  128:  7436 
• 6 Georgy M. Boucard V. Campagne J.-M. J. Am. Chem. Soc.  2005,  127:  14180 
• For Au- or Ag-catalyzed [3,3]-sigmatropic rearrangement of propargylic acetates, see:
• 8a Zhang L. Wang S. J. Am. Chem. Soc.  2006,  128:  1442 
• 8b Zhang L. J. Am. Chem. Soc.  2005,  127:  16804 
• 8c Buzas A. Istrate F. Gagosz F. Org. Lett.  2006,  8:  1957 
• 8d Sromek AW. Kelin AV. Gevorgyan V. Angew. Chem. Int. Ed.  2004,  43:  2280 
• 9a Asao N. Takahashi K. Lee S. Kasahara T. Yamamoto Y. J. Am. Chem. Soc.  2002,  124:  12650 
• 9b Yao T. Zhang X. Larock RC. J. Am. Chem. Soc.  2004,  126:  11164 
• 10 Shah BK. Neckers DC. Chem. Mater.  2006,  18:  603 

7

General experimental procedure (3a): To a mixture of PPh₃ (2.6 mg, 0.01 mmol) and NaAuCl₄·H₂O (3.6 mg, 0.01 mmol) in dry DCE (0.2 mL) under an argon atmosphere at 0 °C was added a solution of yne-propargylic acetate 1a (100 mg, 0.30 mmol) in DCE (1.0 mL). The resulting reaction mixture was stirred at r.t. for 0.5 → 4 h. Upon completion of the reaction, monitored by TLC, the reaction mixture was concentrated in vacuo and the residue was subjected to flash column chromatography (hexane-EtOAc, 20:1) to afford the corresponding product 3a (72.4 mg, 83%); FT-IR (NaCl): 3058, 2961, 2926, 2864, 2362, 2335, 1686, 1627, 1588, 1491, 1452 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ = 8.00 (s, 1 H), 7.93 (d, J = 8.05 Hz, 1 H), 7.88 (d, J = 8.00 Hz, 1 H), 7.85 (s, 1 H), 7.61-7.51 (m, 2 H), 7.48-7.38 (m, 5 H), 2.35 (t, J = 7.4 Hz, 2 H), 1.44 (quint, J = 7.4 Hz, 2 H), 1.18-1.06 (m, 2 H), 0.74 (t, J = 7.4 Hz, 3 H); ¹³C NMR (100 MHz, CDCl₃): δ = 207.88, 141.09, 139.85, 137.45, 134.15, 132.07, 129.49, 129.15, 129.03, 129.89, 128.82, 128.20, 128.04, 127.99, 127.86, 126.96, 42.88, 26,93, 22.36, 13.90; HRMS: m/z calcd for C₂₁H₂₀ONa⁺: 311.1411; found: 311.1402. 3b: FT-IR (NaCl): 2958, 2929, 2864, 1682, 1635, 1593, 1461 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ = 8.48 (s, 1 H), 8.11-7.82 (m, 4 H), 7.58 (dddd, J = 18.31, 8.15, 6.86, 1.37 Hz, 2 H), 3.11 (t, J = 7.4 Hz, 2 H), 1.87-1.70 (m, 2 H), 1.52-1.41 (m, 2 H), 0.99 (t, J = 7.4 Hz, 2 H); ¹³C NMR (100 MHz, CDCl₃): δ = 200.55, 135.47, 134.39, 132.52, 129.71, 129.66, 129.58, 129.55, 129.50, 128.45, 128.35, 128.29, 127.79, 127.73, 126.67, 124.00, 123.94, 38.40, 26.63, 22.52, 13.97; HRMS: m/z calcd for C₁₅H₁₆ONa⁺: 235.1099; found: 235.1102. 3e: FT-IR (NaCl): 3051, 2991, 2957, 2927, 2870, 1687, 1626, 1581, 1506, 1454, 1390 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ = 8.19 (s, 1 H), 8.08-7.82 (m, 5 H), 7.73-7.34 (m, 7 H), 2.31-2.10 (m, 2 H), 1.30-1.13 (m, 2 H), 0.98-0.80 (m, 2 H), 0.58 (t, J = 7.3 Hz, 3 H); ¹³C NMR (100 MHz, CDCl₃): δ = 206.20, 140.32, 139.01, 135.76, 134.19, 133.83, 132.39, 132.32, 130.97, 129.04, 128.60, 128.57, 128.39, 128.22, 128.02, 127.73, 127.11, 126.69, 126.26, 126.06, 125.54, 41.96, 26.69, 22.20, 13.78; HRMS: m/z calcd for C₂₅H₂₂ONa⁺: 361.1568; found: 361.1577. 3f: FT-IR (NaCl): 3056, 2965, 2905, 2865, 1686, 1597, 1485, 1477, 1451, 1362, 1274 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ = 7.88 (ddd, J = 9.37, 7.48, 3.72 Hz, 3 H), 7.62 (s, 1 H), 7.57-7.51 (m, 2 H), 7.50-7.45 (m, 2 H), 7.45-7.33 (m, 3 H), 0.93 (s, 9 H); ¹³C NMR (100 MHz, CDCl₃): δ = 216.76, 141.18, 140.04, 136.40, 133.32, 131.75, 130.11, 130.02, 128.95, 128.83, 128.73, 128.12, 127.82, 127.19, 126.89, 125.17, 45.26, 27.57; HRMS: m/z calcd for C₂₁H₂₀ONa⁺: 311.1412; found: 311.1417. 3h: FT-IR (NaCl): 3059, 1651, 1624, 1597, 1465, 1442, 1380, 1349, 1283, 1233 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ = 8.28 (s, 1 H), 7.99-7.90 (m, 4 H), 7.89-7.85 (m, 2 H), 7.67-7.60 (m, 2 H), 7.59-7.50 (m, 5 H); ¹³C NMR (100 MHz, CDCl₃): δ = 196.97, 138.13, 135.49, 135.05, 132.60, 132.48, 132.09, 130.32, 129.64, 128.71, 128.68, 128.65, 128.56, 128.54, 128.52, 128.04, 127.02, 126.01, 94.70; HRMS: m/z calcd for C₁₇H₁₂ONa⁺: 255.0786; found: 255.0781. 3i: FT-IR (NaCl): 2958, 2928, 2865, 1962, 1754, 1666, 1562, 1466, 1367, 1277, 1205 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ = 8.04 (s, 1 H), 7.98-7.90 (m, 3 H), 7.75-7.68 (m, 2 H), 7.66-7.53 (m, 2 H), 7.49-7.41 (m, 1 H), 7.39-7.28 (m, 5 H), 7.25-7.16 (m, 3 H); ¹³C NMR (100 MHz, CDCl₃): δ = 198.57, 198.53, 140.56, 138.74, 137.93, 137.61, 134.29, 133.06, 131.78, 130.26, 129.67, 129.57, 129.43, 129.31, 128.65, 128.52, 128.35, 128.18, 128.05, 127.44, 127.04; HRMS: m/z calcd for C₂₃H₁₆ONa⁺: 331.1099; found: 331.1110. 3j: FT-IR (NaCl): 3054, 2927, 2861, 2364, 2333, 1662, 1596, 1446, 1280, 1222 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ = 8.18 (s, 1 H), 8.00 (d, J = 10.46 Hz, 2 H), 7.94 (d, J = 7.94 Hz, 1 H), 7.78 (t, J = 8.65, 8.65 Hz, 2 H), 7.72-7.59 (m, 3 H), 7.55-7.50 (m, 2 H), 7.45-7.32 (m, 4 H), 7.32-7.25 (m, 2 H), 7.12 (t, J = 7.82 Hz, 2 H); ¹³C NMR (100 MHz, CDCl₃): δ = 198.11, 138.63, 138.19, 137.86, 136.87, 134.11, 133.58, 132.51, 132.19, 131.98, 130.96, 129.78, 129.69, 128.85, 128.33, 128.29, 128.20, 128.15, 128.11, 128.04, 127.91, 127.17, 126.28, 126.24, 125.87, 125.12; HRMS: m/z calcd for C₂₇H₁₈ONa⁺: 381.1255; found: 381.1263. 7e: FT-IR (NaCl): 3050, 2961, 2934, 2866, 2242, 1937, 1811, 1594, 1489, 1451, 1387, 1315 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ = 8.04 (s, 1 H), 7.98-7.90 (m, 3 H), 7.75-7.68 (m, 2 H), 7.66-7.53 (m, 2 H), 7.49-7.41 (m, 1 H), 7.39-7.28 (m, 5 H), 7.25-7.16 (m, 3 H), 3.10 (m, 2 H), 2.22 (td, J = 12.4, 4.4 Hz, 1 H), 2.08 (dt, J = 12.4, 4.4 Hz, 1 H), 1.23-1.15 (m, 4 H), 0.92 (m, 3 H), 0.51 (t, J = 7.4 Hz, 3 H); ¹³C NMR (100 MHz, CDCl₃): δ = 198.57, 198.53, 140.56, 138.74, 137.93, 137.61, 134.29, 133.06, 131.78, 130.26, 129.67, 129.57, 129.43, 129.31, 128.65, 128.52, 128.35, 128.18, 128.05, 127.44, 127.04; HRMS: m/z calcd for C₂₇H₂₆ONa⁺: 389.1881; found: 389.1890.