Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.

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Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section General methods. NMR spectra were recorded at 400 MHz and 13 C NMR spectra at 100 MHz, with either TMS( =0) or residual CHCl 3 in the CDCl 3 solvent (7.24) as internal standards. J values are reported in Hz. High resolution mass spectra were measured by using FAB method. Flash column chromatography was performed with Kieselgel 60 Art 9385 (230-400 mesh). All sovents used were purified according to standard procedures. Typical procedure : A mixture of 30 mg (0.12 mmol) of 3,5-dibromo-2-pyrone, 52 mg (0.14 mmol) of tributylphenyltin, 7 mg (5 mol%) of Pd( ) 4, 2 mg (10 mol%) of CuI and 1 ml of toluene was heated at 100 for 0.5 h. Upon cooling to rt, the reaction mixture was treated with saturated KF (aq.), diluted with Et 2, and filtered through a plug of Celite. The filtrate was dried over MgS 4, concentrated and purified by column chromatography (hexanes : EtAc = 20 : 1) provided 28 mg of 2a in 94% yield. 5-omo-3-phenyl-pyran-2-one (2a): NMR (400MHz, CDCl 3 ) δ 7.63-7.60 (m, 2H), 7.57 (d, J = 2.4 Hz, 1H), 7.45 (d, J = 2.0 Hz, 1H), 7.43-7.39 (m, 3H); 13 CDCl 3 ) δ 159.2, 148.1, 141.7, 133.2, 129.2, 129.1, 128.4, 128.1, 101.2; FT- 2a IR (CHCl 3 ) 3083, 1727,1609 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 1 8 2 250.9708, found 250.9704. 3-omo-5-phenyl-pyran-2-one (3a): NMR (400MHz, CDCl 3 ) δ 7.99 (d, J = 2.4 Hz, 1H), 7.67 (d, J = 2.4 Hz, 1H), 7.46-7.34 (m, 5H); 13 CDCl 3 ) δ 157.5, 146.8, 144.9, 132.0, 129.1, 128.5, 125.9, 121.3, 112.4 ; FT-IR (CHCl 3 ) 3082, 1728, 1644 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 1 8 2 250.9708, found 250.9690. 3a

5-omo-3-(1-ethoxy-vinyl)-pyran-2-one (2b): NMR (400MHz, CDCl 3 ) δ 7.78 (d, J = 2.8 Hz, 1H), 7.52 (d, J = 2.8 Hz, 1H), 5.73 (d, J = 2.4 Hz, 1H), 4.59 (d, J = 2.4 Hz, 1H), 3.87 (q, J = 6.8 Hz, 2H), 1.39 (t, J = 6.8 Hz, 3H); 13 CDCl 3 ) δ 157.5, 151.1, 147.8, 140.2, 122.6, 101.1, 91.0, 63.1, 5-omo-3-trimethylsilanylethynyl-pyran-2-one (2c): NMR (400MHz, CDCl 3 ) δ 7.67 (d, J = 2.4 Hz, 1H), 7.53 (d, J = 2.4 Hz, 1H), 0.25 (s, 9H); 13 CDCl 3 ) δ 158.1, 148.9, 147.6, 114.2, 104.6, 100.2, 96.5, -0.2; FT-IR (CHCl 3 ) Et 2b 14.5; FT-IR (CHCl 3 ) 3060, 2863, 1721, 1647 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 9 H 10 3 244.9813, found 244.9809. 3-omo-5-(1-ethoxy-vinyl)-pyran-2-one (3b): NMR (400MHz, CDCl 3 ) δ 7.89 (d, J = 2.4 Hz, 1H), 7.77 (d, J = 2.4 Hz, Et 1H), 4.39 (d, J = 4.0 Hz, 1H), 4.23 (d, J = 4.0 Hz, 1H), 3.87 (q, J = 7.2 Hz, 2H), 1.38 (t, J = 7.2 Hz, 3H); 13 3b CDCl 3 ) δ 157.7, 152.8, 147.6, 142.5, 117.2, 111.6, 83.4, 63.7, 14.5; FT-IR (CHCl 3 ) 3035, 2943, 1724, 1647 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 9 H 10 3 244.9813, found 244.9794. 2c TMS 2927, 2150, 1741, 1600 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 10 H 12 2 Si 270.9790, found 270.9789. 5-omo-3-furan-2-yl-pyran-2-one (2d): NMR (400MHz, CDCl 3 ) δ 7.70 (d, J = 2.4 Hz, 1H), 7.50 (d, J = 2.4 Hz, 1H), 7.49 (d, J = 1.2 Hz, 1H), 7.30 (d, J = 3.2 Hz, 1H), 6.50 (dd, J = 3.2, 1.2 Hz, 1H); 13 2d CDCl 3 ) δ 156.8, 146.3, 146.0, 143.8, 135.6, 118.9, 113.6, 112.4, 101.4; FT-IR (CHCl 3 ) 3084, 1739, 1611 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 9 H 5 3 240.9500, found 240.9485. 3-omo-5-furan-2-yl-pyran-2-one (3d): NMR (400MHz, CDCl 3 ) δ 7.98 (d, J = 2.4 Hz, 1H), 7.85 (d, J = 2.4 Hz, 1H), 7.43 (dd, J = 2.0, 0.8 Hz, 1H), 6.48 6.45 (m, 2H); 13 3d CDCl 3 ) δ 157.2, 145.7, 145.1, 142.8, 141.8, 112.8, 112.7, 111.6, 106.4; FT-IR (CHCl 3 ) 3084, 1734, 1611 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 9 H 6 3 240.9500, found 240.9525. 5-omo-3-thiophen-2-yl-pyran-2-one (2e): NMR (400MHz, CDCl 3 ) δ 7.71 (dd, J = 3.6, 1.0 Hz, 1H), 7.62 (d, J = 2.4 Hz, 1H), S 7.52 (d, J = 2.4 Hz, 1H), 7.43 (dd, J = 5.2, 1.0 Hz, 1H), 7.09 (dd, J = 5.2, 3.6 Hz, 1H); 13 2e CDCl 3 ) δ 158.2, 146.6,

137.1, 134.2, 128.6, 127.5, 127.4, 122.9, 101.2 ; FT-IR (CHCl 3 ) 3094, 1714, 1598, 1422 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 9 H 6 2 S 256.9272, found 256.9260. 3-omo-5-thiophen-2-yl-pyran-2-one (3e): NMR (400MHz, CDCl 3 ) δ 7.97 (d, J = 2.0 Hz, 1H), 7.73 (d, J = 2.4 Hz, 1H), 7.31 (dd, J = 5.2, 1.2 Hz, 1H), 7.11 (dd, J = 3.6, 1.2 Hz, 1H), 7.07 (dd, J S = 5.2, 3.6 Hz, 1H); 13 3e CDCl 3 ) δ 156.9, 145.4, 143.8, 133.6, 127.8, 125.5, 124.3, 115.6, 112.4 ; FT-IR (CHCl 3 ) 3164, 1720, 1515 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 9 H 6 2 S 256.9272, found 256.9090. 5-omo-3-pyridin-2-yl-pyran-2-one (2f): NMR (400MHz, CDCl 3 ) δ 8.64-8.62 (m, 1H), 8.47 (d, J = 3.2 Hz, 1H), 8.37 (d, J = N 8.0 Hz, 1H), 7.76 (td, J = 8.0, 2.0 Hz, 1H), 7.66 (d, J = 2.8, 1H), 7.28 (ddd, J = 7.2, 4.8, 1.2 Hz, 1H); 13 2f CDCl 3 ) δ 159.1, 149.6, 149.3, 149.2, 144.4, 136.6, 125.8, 123.7, 123.6, 101.9; FT-IR (CHCl 3 ) 3067, 1726, 1653 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 10 H 7 N 2 251.9660, found 251.9659. 3-omo-5-pyridin-2-yl-pyran-2-one (3f): NMR (400MHz, CDCl 3 ) δ 8.63-8.61 (m, 1H), 8.49 (d, J = 2.4 Hz, 1H), 8.13 (d, J = N 2.4 Hz, 1H), 7.75 (td, J = 8.0, 2.0 Hz, 1H), 7.48 (d, J = 8.0 Hz, 1H), 7.27 (ddd, J = 7.9, 4.8, 1.2 Hz,, 1H); 13 3f CDCl 3 ) δ 157.6, 149.8, 149.7, 148.9, 143.6, 137.1, 123.1, 120.4, 118.9, 112.3 ; FT-IR (CHCl 3 ) 3067, 1724, 1654 cm -1 ; HRMS (FAB) m/z (M+1) ) calcd for C 10 H 7 N 2 251.9660, found 251.9674. 4-(5-omo-2-oxo-2H-pyran-3-yl)-benzonitrile (2g): NMR (400MHz, CDCl 3 ) δ 7.78 7.76 (m, 2H), 7.72 7.70 (m, 2H), 7.65 (d, J = 2.4 Hz, 1H), 7.54 (d, J = 2.4 Hz, 1H); 13 C NMR (100MHz, CDCl 3 ) δ 158.6, 149.4, 143.3, 137.5, 132.1, 128.7, 127.1, 118.2, 112.9, 101.0 ; FT-IR (CHCl 3 ) 3049, 2226, 1714, 1601 cm -1 ; HRMS (FAB) m/z (M+1) ) calcd for C 12 H 7 N 2 275.9660, found 275.9672. 4-(5-omo-6-oxo-6H-pyran-3-yl)-benzonitrile (3g): 2g CN NMR (400MHz, CDCl 3 ) δ 7.98 (d, J = 2.0 Hz, 1H), 7.76 (d, J = 2.0 Hz, 1H), 7.75 7.73 (m, 2H), 7.51 7.48 (m, 2H); 13 C NMR (100MHz, CDCl 3 ) δ 156.9, 147.9, 143.6, 136.7, 133.0, 126.5, 119.8, 117.9, 113.3, 112.5 ; FT-IR (CHCl 3 ) 3008, 2232, NC 3g 1737, 1629 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 12 H 7 N 2 275.9660, found 275.9661.

4-(5-omo-2-oxo-2H-pyran-3-yl)-benzoic acid methyl ester (2h): NMR (400MHz, CDCl 3 ) δ 8.01 8.06 (m, 2H), 7.73 7.70 (m, 2H), 7.61 (d, J = 2.4 Hz, 1H), 7.52 (d, J = 2.4 Hz, 1H), 3.93 (s, 3H); 13 CDCl 3 ) δ 166.2, 158.9, 148.9, 142.8, 137.4, 130.6, 129.6, 2h C 2 Me 128.1, 128.0, 101.1, 52.4 ; FT-IR (CHCl 3 ) 3150, 1728, 1613 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 13 H 10 4 308.9762, found 308.9761. 4-(5-omo-6-oxo-6H-pyran-3-yl)-benzoic acid methyl ester (3h): NMR (400MHz, CDCl 3 ) δ 8.11 8.09 (m, 2H), 8.02 (d, J = 2.4 Hz, 1H), 7.76 (d, J = 2.4 Hz, 1H), 7.46 7.43 (m, 2H), 3.94 (s, 3H); 13 CDCl 3 ) δ 166.0, 157.2, 147.6, 144.2, 136.5, 130.5, 130.2, 125.8, Me 2 C 3h 120.4, 112.9, 52.4 ; FT-IR (CHCl 3 ) 3073, 1739, 1715, 1616 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 13 H 10 4 308.9762, found 308.9751. 5-omo-3-(4-methoxy-phenyl)-pyran-2-one (2i): NMR (400MHz, CDCl 3 ) δ 7.61 7.59 (m, 2H), 7.54 (d, J = 2.4 Hz, 1H), 7.40 (d, J = 2.4 Hz, 1H), 6.94 6.92 (m, 2H), 3.84 (s, 3H); 13 CDCl 3 ) δ 160.3, 159.6, 147.3, 140.3, 129.5, 128.7, 125.5, 113.9, 101.4, 55.4; FT- IR (CHCl 3 ) 3084, 2943, 1725, 1610 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 12 H 10 3 280.9813, found 280.9812. 3-omo-5-(4-methoxy-phenyl)-pyran-2-one (3i): NMR (400MHz, CDCl 3 ) δ 7.96 (d, J = 2.4 Hz, 1H), 7.61 (d, J = 2.4 Hz, 1H), 7.28 7.26 (m, 2H), 6.96 6.93 (m, 2H), 3.84 (s, 3H); 13 Me CDCl 3 ) δ 159.7, 157.6, 146.0, 145.1, 127.1, 124.3, 121.0, 114.5, 112.2, 55.3 ; FT- 2i Me 3i IR (CHCl 3 ) 3078, 2943, 1725, 1618 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 12 H 10 3 280.9813, found 280.9810. 3-omo-5-vinyl-pyran-2-one (3j): NMR (400MHz, CDCl 3 ) δ 7.95 (d, J = 2.4 Hz, 1H), 7.47 (d, J = 2.4 Hz, 1H), 6.33 (dd, J = 17.6, 11.2 Hz, 1H), 5.52 (d, J = 17.6 Hz, 1H), 5.31 (d, J = 11.2 Hz, 1H) ; 13 3j CDCl 3 ) δ 157.5, 147.9, 141.4, 127.0, 118.3, 115.2, 112.9 ; FT-IR (CHCl 3 ) 3191, 1718, 1651 cm -1 ; HRMS (FAB) m/z (M+1) calcd for C 7 H 6 2 200.9551, found 200.9566. 3-Pallado-5-bromo-2-pyrone (5a; Pd-): NMR (400MHz, CDCl 3 ) δ 7.71 7.66 (m, 12H), 7.37 7.30 (m, 18H), 6.53 6.51 (m, 1H), 6.37 (d, J = 2.4 Hz, 1H); 13 C

NMR (100MHz, CDCl 3 ) δ 160.8 (t, J = 3.0 Hz), 153.6 (t, J = 6.0 Hz), 147.1 (t, J = 5.3 Hz), 143.0, 134.6 (t, J = 6.z), 130.35 (t, J = 23.5 Hz), 130.2, 127.9 (t, J = 5.3 Hz), 101.1.; FT-IR (CHCl 3 ) 3061.0, 3011.1, 1716.5, 1688.3, 1598.0, 1481.6, 1435.1 cm -1 RTEP representation of the X-ray crystal structure of 5a Pd 5a

3-Pallado-5-bromo-2-pyrone (5b; Pd-I): NMR (400MHz, CDCl 3 ) δ 7.71 7.66 (m, 12H), 7.37 7.30 (m, 18H), 6.53 6.51 (m, 1H), 6.37 (d, J = 2.4 Hz, 1H); 13 CDCl 3 ) δ 160.8 (t, J = 3.0 Hz), 153.6 (t, J = 6.0 Hz), 147.1 (t, J = 5.3 Hz), 143.0, 134.6 (t, J = 6.z), 130.35 (t, J = 23.5 Hz), 130.2, 127 Pd I 5b RTEP representation of the X-ray crystal structure of 5b

5-Pallado-3-bromo-2-pyrone (6): NMR (400MHz, CDCl 3 ) δ 7.68 7.63 (m, 12H), 7.42 7.33 (m, 18H), 6.48 (dd, J = 1.2, 0.8 Hz, 1H), 6.26 (dd, J = 1.2, 0.8 Hz, 1H); 13 CDCl 3 ) δ 158.3, 150.4, 143.9, 134.5 (t, J = 6.4 Hz), 130.7, 129.8 (t, J = 23.9 Hz), 128.3 (t, J = 5.3 Hz), 125.2, 110.5; FT-IR (CHCl 3 ) 3057.0, 1732.8, 1717.2, 1704.6, 1482.4, 1435.4 cm -1. RTEP representation of the X-ray crystal structure of 6 Pd Ph 3 P 6

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