Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information
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- Αφροδίσιος Αντωνόπουλος
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1 Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans Liang Yun, Shi Tang, Xu-Dong Zhang, Li-Qiu Mao, Ye-Xiang Xie and Jin-Heng Li* Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha , China Supporting Information List of Contents (A) Materials (B) Typical experimental procedure S2 S2 (C) Analytical data for 2, 3 and 4 S2-9 (D) References S9 (E) Spectra S10-49 S1
2 (A) Materials: 2-Alkynylphenols 1a g were prepared from the reaction of the corresponding 2-iodophenols with terminal alkynes by known procedures. 1 (B) Typical experimental procedure (1) Typical experimental procedure for the palladium-catalyzed annulation of 2-(2-n-octylethynyl)phenol (1a) to form 2-octylbenzofuran (2a). A mixture of 2-alkynylphenol 1a (0.3 mmol), PdX 2 (5 mol %) and DCE (5 ml) was stirred at room temperature for the indicated time until complete consumption of starting material as judged by TLC and GC analysis. Then the mixture was filtered and evaporated, the residue was purified by flash column chromatography to afford 2a (hexane/ethyl acetate). (2) Typical experimental procedure for the synthesis of 2-substituted 3-halobenzo[b]furans 3 and 4. A mixture of 2-alkynylphenol 1 (0.3 mmol), PdX 2 (5 10 mol %), CuX 2 (3 equiv), HEt 3 NX (0.2 equiv) and DCE (5 ml) was stirred at the indicated reaction temperature for 6-24 h until complete consumption of starting material as judged by TLC and GC analysis. Then the mixture was filtered and evaporated, the residue was purified by flash column chromatography to afford 3 or 4 (hexane/ethyl acetate). (C) Analytical data for 2, 3 and 4 S2
3 2-octylbenzofuran (2a): Colorless oil; 1 H NMR (400 MHz) δ: 7.48 (d, J = 8.0 Hz, 1H), 7.41 (d, J = 8.4 Hz, 1H), (m, 2H), 6.37 (s, 1H), 2.76 (t, J = 7.6 Hz, 2H), (m, 2H), (m, 10H), 0.88 (t, J = 6.8 Hz, 3H); 13 C NMR (100 MHz) δ: 159.8, 154.6, 129.0, 123.0, 122.3, 120.1, 110.7, 101.7, 31.8, 29.3, 29.2, 28.4, 27.7, 22.7, 14.1; LRMS (EI, 20 ev) m/z (%): 230 (M +, 64), 187 (11), 173 (8), 145 (13), 131 (100) ; HRMS (EI) for C 16 H 22 O (M + ): calcd , found phenylbenzofuran (2b) 1 : White solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 7.87 (d, J = 7.2 Hz, 2H), 7.58 (d, J = 7.6 Hz, 1H), 7.52 (d, J = 8.0 Hz, 1H), 7.45 (t, J = 7.2 Hz, 2H), 7.33 (t, J = 7.2 Hz, 1H), 7.28 (t, J = 7.2 Hz, 1H), 7.23 (t, J = 7.2 Hz, 1H), 7.03 (s, 1H); 13 C NMR (100 MHz) δ: 155.9, 154.9, 130.4, 129.2, 128.8, 128.5, 124.9, 124.2, 122.9, 120.9, 111.2, 101.3; LRMS (EI, 20 ev) m/z (%): 194 (M +, 100); 2-p-tolylbenzofuran (2c) 2 : White solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 7.76 (d, J = 8.0 Hz, 2H), 7.57 (d, J = 8.4 Hz, 1H), 7.51 (d, J = 7.6 Hz, 1H), (m, 4H), 6.97 (s, 1H), 2.40 (s, 3H); 13 C NMR (100 MHz) δ: 156.2, 154.8, 138.6, 129.5, 129.4, 127.8, 124.9, 124.0, 122.9, 120.8, 111.1, 100.6, 21.4; LRMS (EI, 20 ev) m/z (%): 208 (M +, 100). 2-tert-butylbenzofuran (2d) 3 : Colorless oil; 1 H NMR (400 MHz) δ: 7.48 (d, J = 8.8 Hz, 1H), 7.41 (d, J = 7.6 Hz, 1H), (m, 2H), 6.35 (s, 1H), 1.38 (s, 9H); S3
4 13 C NMR (100 MHz) δ: 167.4, 154.5, 128.8, 123.0, 122.2, 120.3, 110.7, 98.9, 31.6, 28.8; LRMS (EI, 20 ev) m/z (%): 174 (M +, 23), 159 (100). 6-methyl-2-phenylbenzofuran (2e) 3, 4 : White solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 7.84 (d, J = 7.6 Hz, 2H), 7.44 (t, J = 8.0 Hz, 3H), 7.33 (t, J = 7.2 Hz, 2H), 7.06 (d, J = 8.0 Hz, 1H), 6.97 (s, 1H), 2.48 (s, 3H); 13 C NMR (100 MHz) δ: 155.3, 155.2, 134.5, 130.6, 128.7, 128.2, 126.6, 124.7, 124.3, 120.3, 111.4, 101.2, 21.8; LRMS (EI, 20 ev) m/z (%): 208 (M +, 100). 5,7-dichloro-2-phenylbenzofuran (2f) 3, 4 : White solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 7.86 (d, J = 7.6 Hz, 2H), (m, 4H), 7.26 (s, 1H), 6.96 (s, 1H); 13 C NMR (100 MHz) δ:158.1, 149.2, 131.4, 129.4, 129.3, 128.9, 128.6, 125.2, 124.2, 119.0, 117.1, 101.1; LRMS (EI, 20 ev) m/z (%): 262 (M +, 100). 5-nitro-2-phenylbenzofuran (2g) 3, 4 : Yellow solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 8.51 (s, 1H), 8.22 (d, J = 8.8 Hz, 1H), 7.88 (d, J = 7.6 Hz, 2H), 7.60 (d, J = 8.8 Hz, 1H), 7.50 (t, J = 7.2 Hz, 2H), 7.43 (t, J = 7.6 Hz, 1H), 7.14 (s, 1H); 13 C NMR (100 MHz) δ:159.2, 157.6, 144.3, 129.7, 129.6, 129.1, 129.0, 125.2, 120.1, 117.3, 111.4, 101.6; LRMS (EI, 20 ev) m/z (%): 239 (M +, 100). S4
5 2-octyl-3-bromobenzofuran (3a): Colorless oil; 1 H NMR (400 MHz) δ: (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 10H), 0.87 (t, J = 6.8 Hz, 3H); 13 C NMR (100 MHz) δ: 155.9, 128.3, 124.3, 123.1, 120.7, 119.1, 111.0, 94.1, 31.8, 29.2, 27.9, 27.8, 27.5, 26.6, 22.6, 14.1; LRMS (EI, 20 ev) m/z (%): 310 (M + + 2, 60), 308 (M +, 58), 229 (M + - Br, 100); HRMS (EI) for C 16 H BrO (M + ): calcd , found phenyl-3-bromobenzofuran (3b): White solid, o C; 1 H NMR (400 MHz) δ: 8.17 (d, J = 8.4 Hz, 2H), (m, 7H); 13 C NMR (100 MHz) δ: 153.1, 150.3, 129.6, 129.5, 129.0, 128.6, 126.7, 125.6, 123.5, 119.9, 111.3, 93.8; LRMS (EI, 20 ev) m/z (%): 274 (M + + 2, 98), 272 (M +, 100), 195 (M + - Br, 19); HRMS (EI) for C 14 H 79 9 BrO (M + ): calcd , found p-tolyl-3-bromobenzofuran (3c): White solid, mp o C; 1 H NMR (400 MHz) δ: 8.06 (d, J = 8.8 Hz, 2H), 7.54 (d, J = 8.8 Hz, 1H), 7.50 (d, J = 8.8 Hz, 1H), (m, 4H), 2.41 (s, 3H); 13 C NMR (100 MHz) δ: 153.0, 150.6, 139.2, 129.5, 129.3, 126.7, 125.3, 123.4, 119.7, 111.2, 93.1, 21.5; LRMS (EI, 20 ev) m/z (%): 288 (M + + 2, 97), 286 (M +, 100), 207 (M + - Br, 17); HRMS (EI) for C 15 H BrO (M + ): calcd , found tert-butyl-3-bromobenzofuran (3d): Colorless oil; 1 H NMR (400 MHz) δ: 7.46 (d, J = 8.8 Hz, 1H), 7.41 (d, J = 8.8 Hz, 1H), (m, 2H), 1.51 (s, 9H); 13 C S5
6 NMR (100 MHz) δ: 160.0, 152.3, 129.5, 124.4, 122.9, 119.2, 110.9, 91.2, 34.3, 28.9; LRMS (EI, 20 ev) m/z (%): 254 (M + + 2, 21), 252 (M +, 23), 239 (100), 237 (90), 158 (M + - CH 3 - Br, 36); HRMS (EI) for C 12 H BrO (M + ): calcd , found bromo-6-methyl-2-phenylbenzofuran (3e): White solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 8.13 (d, J = 8.0 Hz, 2H), 7.46 (t, J = 7.6 Hz, 2H), (m, 2H), 7.27 (s, 1H), 7.10 (d, J = 7.6 Hz, 1H), 2.47 (s, 3H); 13 C NMR (100 MHz) δ:153.4, 149.5, 136.0, 129.6, 128.7, 128.5, 127.1, 126.5, 124.8, 119.3, 111.4, 93.7, 21.6; LRMS (EI, 20 ev) m/z (%): 288 (M + + 2, 100), 286 (M +, 98), 207 (M + - Br 12), 178 (40), 103 (12), 89 (21), 76 (21); HRMS (EI) for C 15 H BrO (M + ): calcd , found bromo-5,7-dichloro-2-phenylbenzofuran (3f): White solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 8.17 (d, J = 8.0 Hz, 2H), (m, 4H), (m, 1H); 13 C NMR (100 MHz) δ:152.7, 147.6, 131.9, 129.9, 129.4, 128.7, 128.5, 127.0, 125.6, 118.2, 117.4, 93.0; LRMS (EI, 20 ev) m/z (%): 344 (M + + 4, 44), 342 (M + + 2, 100), 340 (M +, 62), 233 (51), 263 (20), 261 (M + - Br, 32), 228 (8), 226 (M + - Br - Cl, 24), 163 (64), 116 (24), 98 (29), 81 (29); HRMS (EI) for C 14 H 7 Cl 79 2 BrO (M + ): calcd , found S6
7 3-bromo-5-nitro-2-phenylbenzofuran (3g): Pale yellow solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 8.44 (s, 1H), 8.25 (d, J = 8.8 Hz, 1H), 8.14 (d, J = 8.4 Hz, 2H), 7.57 (d, J = 9.2 Hz, 1H), (m, 3H); 13 C NMR (100 MHz) δ: 155.8, 153.6, 144.6, 130.2, 130.1, 128.8, 128.3, 126.9, 121.2, 116.5, 111.8, 93.8; LRMS (EI, 20 ev) m/z (%): 319 (M + + 2, 97), 317 (M +, 100), 238 (M + - Br, 16); HRMS (EI) for C 14 H 79 8 BrNO 3 (M + ): calcd , found octyl-3-chlorobenzofuran (4a): Colorless oil; 1 H NMR (400 MHz) δ: 7.38 (d, J = 8.0 Hz, 1H), (m, 1H), (m, 2H), 2.85 (t, J = 7.6 Hz, 2H), (m, 2H), (m, 10H), 0.88 (t, J = 7.4 Hz, 3H); 13 C NMR (100 MHz) δ: 159.2, 154.2, 131.0, 124.4, 124.2, 123.1, 120.7, 110.9, 31.8, 29.3, 29.2, 29.0, 27.9, 27.8, 22.7, 14.1; LRMS (EI, 20 ev) m/z (%): 266 (M + + 2, 17), 264 (M +, 48), 229 (M + - Cl, 27), 165 (100); HRMS (EI) for C 16 H ClO (M + ): calcd , found phenyl-3-chlorobenzofuran (4b): White solid, mp o C; 1 H NMR (400 MHz) δ: 8.20 (d, J = 8.8 Hz, 2H), (m, 5H), (m, 2H); 13 C NMR (100 MHz) δ: 153.9, 153.0, 132.4, 130.0, 129.2, 128.5, 127.6, 125.7, 123.5, 121.8, 111.2; LRMS (EI, 20 ev) m/z (%): 230 (M + + 2, 43), 228 (M +, 100), 193 (M + - Cl, 28); HRMS (EI) for C 14 H 35 9 ClO (M + ): calcd , found p-tolyl-3-chlorobenzofuran (4c): White solid, m.p o C; 1 H NMR (400 MHz) δ: 8.07 (d, J = 8.8 Hz, 2H), (m, 2H), (m, 4H), 2.43 (s, S7
8 3H); 13 C NMR (100 MHz) δ: 153.8, 153.3, 139.4, 132.5, 129.2, 127.4, 127.2, 125.4, 123.4, 121.7, 111.1, 21.5; LRMS (EI, 20 ev) m/z (%): 244 (M + + 2, 41), 242 (M +, 100), 207 (M + - Cl, 32); HRMS (EI) for C 15 H ClO (M + ): calcd , found tert-butyl-3-chlorobenzofuran (4d): Colorless oil; 1 H NMR (400 MHz) δ: 7.50 (d, J = 8.8 Hz, 1H), (m, 1H), (m, 2H), 1.49 (s, 9H); 13 C NMR (100 MHz) δ: 158.8, 151.9, 128.1, 124.3, 122.8, 118.3, 111.0, 110.7, 34.1, 28.7; LRMS (EI, 20 ev) m/z (%): 210 (M + + 2, 8), 208 (M +, 25), 193 (100), 158 (M + - CH 3 - Cl, 20); HRMS (EI) for C 12 H ClO (M + ): calcd , found chloro-6-methyl-2-phenylbenzofuran (4e): White solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 8.16 (d, J = 7.6 Hz, 1H), 8.11 (d, J = 8.0 Hz, 1H), (m, 5H), 7.11 (d, J = 8.0 Hz, 1H), 2.50 (s, 3H); 13 C NMR (100 MHz) δ: 153.1, 148.3, 136.0, 129.5, 128.7, 128.6, 126.4, 126.2, 126.1, 124.8, 118.4, 111.6, 21.8; LRMS (EI, 20 ev) m/z (%): 244 (M + + 2, 34), 242 (M +, 100), 207 (M + - Cl, 12), 178 (61), 152 (20), 103 (43), 89 (42), 76 (65); HRMS (EI) for C 15 H ClO (M + ): calcd , found ,5,7-trichloro-2-phenylbenzofuran (4f): White solid, mp o C (uncorrected); 1 H NMR (400 MHz) δ: 8.19 (d, J = 8.4 Hz, 2H), (m, 4H), 7.36 (d, J = 7.6 Hz, 2H); 13 C NMR (100 MHz) δ: 155.4, 148.2, 134.8, 130.0, 128.9, 128.6, 127.7, S8
9 125.5, 125.2, 120.2, 119.0, 101.2; LRMS (EI, 20 ev) m/z (%): 298 (M + + 2, 7), 296 (M +, 8), 263 (46), 261 (M + - Cl, 71), 233 (74), 226 (M + - 2Cl, 38), 194 (M + - 3Cl, 20), 163 (100), 81 (46); HRMS (EI) for C 14 H 35 7 Cl 3 O (M + ): calcd , found (C) References (1) (a) Arcadi, A.; Marinelli, F. Synthesis 1986, 749. (b) Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, (2) Chatterjea, J. N.; Roy, S. K. J. Indian. Chem. Soc. 1957, 34, 98. (3) Karakhanov, E. A.; Drovyannikova, G. V.; Viktorova, E. A. Khim. Get. Soedin 1974, 175. (4) (a) Kundu, N. G.; Pal.; M.; Mahanty, J. S.; Dasgupta, S. K. J. Chem. Soc., Chem. Commun. 1992, 41. (b) Torii, S.; Xu, L. H.; Okumoto, H. Synlett 1992, 515. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, (d) Candiani, I.; Debernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269. (e) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, (f) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, (g) Bishop, B. C.; Cottrell, I. F.; Hands, D. Synthesis 1997, (h) Kundu, N. G.; Pal, M.; Mahanty, J. S.; De, M. J. Chem. Soc., Perkin Trans , (i) Lutjens, H.; Scammells, P. J. Synlett 1999, (j) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 667, S9
10 (D) Spectra O n octyl 2-octylbenzofuran (2a) S10
11 O n octyl 2-octylbenzofuran (2a) S11
12 O 2-phenylbenzofuran (2b) S12
13 O 2-phenylbenzofuran (2b) S13
14 O Me 2-p-tolylbenzofuran (2c) S14
15 O Me 2-p-tolylbenzofuran (2c) S15
16 O t Bu 2-tert-butylbenzofuran (2d) S16
17 O t Bu 2-tert-butylbenzofuran (2d) S17
18 O 6-methyl-2-phenylbenzofuran (2e) S18
19 O 6-methyl-2-phenylbenzofuran (2e) S19
20 Cl Cl O 5,7-dichloro-2-phenylbenzofuran (2f) S20
21 Cl Cl O 5,7-dichloro-2-phenylbenzofuran (2f) S21
22 O 2 N O 5-nitro-2-phenylbenzofuran (2g) S22
23 O 2 N O 5-nitro-2-phenylbenzofuran (2g) S23
24 O Br n octyl 2-octyl-3-bromobenzofuran (3a) S24
25 O Br n octyl 2-octyl-3-bromobenzofuran (3a) S25
26 Br O 2-phenyl-3-bromobenzofuran (3b) S26
27 Br O 2-phenyl-3-bromobenzofuran (3b) S27
28 O Br Me 2-p-tolyl-3-bromobenzofuran (3c) S28
29 O Br Me 2-p-tolyl-3-bromobenzofuran (3c) S29
30 O Br t Bu 2-tert-butyl-3-bromobenzofuran (3d) S30
31 O Br t Bu 2-tert-butyl-3-bromobenzofuran (3d) S31
32 Br O 3-bromo-6-methyl-2-phenylbenzofuran (3e) S32
33 Br O 3-bromo-6-methyl-2-phenylbenzofuran (3e) S33
34 Cl Br Cl O 3-bromo-5,7-dichloro-2-phenylbenzofuran (3f) S34
35 Cl Br Cl O 3-bromo-5,7-dichloro-2-phenylbenzofuran (3f) S35
36 O 2 N Br O 3-bromo-5-nitro-2-phenylbenzofuran (3g) S36
37 O 2 N O Br 3-bromo-5-nitro-2-phenylbenzofuran (3g) S37
38 O Cl n octyl 2-octyl-3-chlorobenzofuran (4a) S38
39 O Cl n octyl 2-octyl-3-chlorobenzofuran (4a) S39
40 Cl O 2-phenyl-3-chlorobenzofuran (4b) S40
41 Cl O 2-phenyl-3-chlorobenzofuran (4b) S41
42 O Cl Me 2-p-tolyl-3-chlorobenzofuran (4c) S42
43 O Cl Me 2-p-tolyl-3-chlorobenzofuran (4c) S43
44 O Cl t Bu 2-tert-butyl-3-chlorobenzofuran (4d) S44
45 O Cl t Bu 2-tert-butyl-3-chlorobenzofuran (4d) S45
46 Cl O 3-chloro-6-methyl-2-phenylbenzofuran (4e) S46
47 Cl O 3-chloro-6-methyl-2-phenylbenzofuran (4e) S47
48 Cl Cl Cl O 3,5,7-trichloro-2-phenylbenzofuran (4f) S48
49 Cl Cl Cl O 3,5,7-trichloro-2-phenylbenzofuran (4f) S49
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