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3. For recent selected examples of gold-catalyzed hydroalkoxylation, see: (a)
Barluenga, J.; Fernández, A.; Diéguez, A.; Rodríguez, F.; Fañanás, F. J. Chem. Eur.
J. 2009, 15, 11660–11667; (b) Diéguez-Vázquez, A.; Tzschucke, C. C.; Crecente-
Campo, J.; McGrath, S.; Ley, S. V. Eur. J. Org. Chem. 2009, 1698–1706; (c) Hirai,
T.; Hamasaki, A.; Nakamura, A.; Tokunaga, M. Org. Lett. 2009, 11, 5510–5513;
(d) Cui, D.-M.; Zheng, Z.-L.; Zhang, C. J. Org. Chem. 2009, 74, 1426–1427; (e)
Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2009, 11, 2079–2081; (f) Paton, R. S.;
Maseras, F. Org. Lett. 2009, 11, 2237–2240; (g) Hadfield, M. S.; Lee, A.-L. Org.
Lett. 2010, 12, 484–487; (h) Horino, Y.; Takata, Y.; Hashimoto, K.; Kuroda, S.;
Kimura, M.; Tamaru, Y. Org. Biomol. Chem. 2008, 6, 4105–4107; (i) Cui, D.-M.;
Yu, K.-R.; Zhang, C. Synlett 2009, 1103–1106.
4. For our previous Pd-catalyzed hydrofunctionalizations of alkynes, see: (a)
Kadota, I.; Shibuya, A.; Lutete, M. L.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4570–
4571; (b) Lutete, M. L.; Kadota, I.; Shibuya, A.; Yamamoto, Y. Heterocycles 2002,
58, 347–357; (c) Lutete, L. M.; Kadota, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004,
126, 1622–1623; (d) Patil, N. T.; Wu, H.; Kadota, I.; Yamamoto, Y. J. Org. Chem.
2004, 69, 8745–8750; (e) Patil, N. T.; Pahadi, N. K.; Yamamoto, Y. Tetrahedron
Lett. 2005, 46, 2101–2103; (f) Kadota, I.; Shibuya, A.; Gyoung, Y. S.; Yamamoto,
Y. J. Am. Chem. Soc. 1998, 120, 10262–10263; (g) Patil, N. T.; Kadota, I.; Shibuya,
A.; Gyoung, Y. S.; Yamamoto, Y. Adv. Synth. Catal. 2004, 346, 800–804; (h) Patil,
N. T.; Yamamoto, Y. J. Org. Chem. 2004, 19, 6478–6481; (i) Kadota, I.; Lutete, M.
L.; Shibuya, A.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6207–6210; (j) Patil, N.
T.; Khan, N. F.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 8497–8499; (k) Patil, N.
T.; Lutete, L. M.; Wu, H.; Pahadi, N. K.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem.
2006, 71, 4270–4279; (l) Patil, N. T.; Huo, Z.; Bajracharya, G. B.; Yamamoto, Y. J.
Org. Chem. 2006, 71, 3612–3614; (m) Bajracharya, G. B.; Huo, Z.; Yamamoto, Y.
J. Org. Chem. 2005, 70, 4883–4886; (n) Huo, Z.; Patil, N. T.; Jin, T.; Pahadi, N. K.;
Yamamoto, Y. Adv. Synth. Catal. 2007, 349, 680–684.
11. Compound 3a: White solid; mp 103.5 °C; 1H NMR (CDCl3, 400 MHz) d 7.61–7.65
(m, 4H), 7.24–7.42 (m, 11H), 3.19 (s, 2H), 1.29 (s, 3H); 13C NMR (CDCl3, 100 MHz)
d 136.8, 136.3, 132.1, 131.2, 128.9, 128.5, 127.7, 126.7, 63.7, 48.1, 27.7; IR (neat)
1471, 1451, 1303, 1085, 1022, 746, 701, 690 cmꢀ1; HRMS (ESI) Calcd for
C21H20S2Na (M+Na) 359.0899. Found 359.0897.
Compound 3b: White solid; mp 75 °C; 1H NMR (CDCl3, 400 MHz) d 7.60–7.64 (m,
4H), 7.32–7.42 (m, 6H), 7.18–7.24 (m, 2H), 6.94–7.00 (m, 2H), 3.15 (s, 2H), 1.26 (s,
3H); 13C NMR (CDCl3, 100 MHz) d 161.8 (J = 235 Hz), 136.8, 132.6 (J = 8.3 Hz),
131.9 (J = 3.3 Hz), 131.8, 129.0, 128.5, 114.5 (J = 21.6 Hz), 63.5, 47.3, 27.6; IR
(neat) 1506, 1471, 1436, 1220, 1056, 854, 774, 703, 691 cmꢀ1; HRMS (ESI) Calcd
for C21H19FS2Na (M+Na) 377.0804. Found 377.0803.
Compound 3c: White solid; mp 93.5 °C; 1H NMR (CDCl3, 400 MHz) d 7.58–7.64
(m, 4H), 7.32–7.42 (m, 6H), 7.23–7.25 (m, 2H), 7.16–7.22 (m, 2H), 3.12 (s, 2H),
1.25 (s, 3H); 13C NMR (CDCl3, 100 MHz) d 136.8, 134.7, 132.7, 132.4, 131.8, 129.1,
128.6, 127.8, 63.4, 47.4, 27.6; IR (neat) 1487, 1469, 1435, 1092, 845, 801, 754,
702, 691 cmꢀ1; HRMS (ESI) Calcd for C21H19ClS2Na (M+Na) 393.0509. Found
393.0507.
Compound 3d: White solid; mp 92 °C; 1H NMR (CDCl3, 400 MHz) d 7.60–7.66 (m,
4H), 7.22–7.40 (m, 6H), 7.08–7.18 (m, 4H), 3.15 (s, 2H), 2.35 (s, 3H), 1.30 (s, 3H).
13C NMR (CDCl3, 100 MHz) d 136.8, 136.3, 133.2, 132.1, 131.0, 128.9, 128.5,
128.4, 63.8, 47.7, 27.7, 21.2; IR (neat) 1510, 1470, 1435, 1064, 1022, 754, 702,
690 cmꢀ1. HRMS (ESI) Calcd for C22H22S2Na (M+Na) 373.1055. Found 373.1054.
Compound 3e: Colorless oil; 1H NMR (CDCl3, 400 MHz) d 7.36–7.46 (m, 4H),
7.06–7.24 (m, 8H), 3.12 (s, 2H), 2.35 (s, 9H), 1.30 (s, 3H); 13C NMR (CDCl3,
100 MHz) d 138.1, 137.4, 136.2, 133.8, 133.4, 131.9, 131.1, 129.7, 128.4, 128.2,
63.6, 47.9, 27.7, 21.3, 21.2; IR (neat) 1572, 1473, 1444, 1056, 806, 779, 693 cmꢀ1
HRMS (ESI) Calcd for C24H26S2Na (M+Na) 401.1368. Found 401.1365.
;
Compound 3f: White solid; mp 133.5 °C; 1H NMR (CDCl3, 400 MHz) d 7.45–7.55
(m, 4H), 7.21–7.30 (m, 5H), 7.10–7.17 (m, 4H), 3.15 (s, 2H), 2.38 (s, 6H), 1.26 (s,
3H); 13C NMR (CDCl3, 100 MHz) d 139.1, 136.9, 136.5, 131.2, 129.3, 128.6, 127.6,
126.7, 63.4, 48.0, 27.5, 21.4; IR (neat) 1489, 1450, 1063, 1017, 815, 754, 704,
679 cmꢀ1; HRMS (ESI) Calcd for C23H24S2Na (M+Na) 387.1212. Found 387.1210.
Compound 3g: White solid; mp 66 °C; 1H NMR (CDCl3, 400 MHz) d 7.36–7.46 (m,
4H), 7.10–7.30 (m, 9H), 3.20 (s, 2H), 2.32 (s, 6H), 1.30 (s, 3H); 13C NMR (CDCl3,
100 MHz) d 138.2, 137.4, 136.5, 133.9, 131.8, 131.2, 129.7, 128.2, 127.6, 126.7,
5. (a) Ulman, A. Chem. Rev. 1996, 96, 1533–1554; (b) Gronbeck, H.; Curioni, A.;
Andreoni, W. J. Am. Chem. Soc. 2000, 122, 3839–3842; (c) Fujita, K.; Nakamura,
N.; Ohno, H.; Leigh, B. S.; Niki, K.; Gray, H. B.; Richards, J. H. J. Am. Chem. Soc.
2004, 126, 13954–13961.
6. (a) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205–3220; (b) Alonso, F.;
Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079–3159; (c) Han, L.-B.; Zhang,
C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080–5081; (d) Cao, C.;
Fraser, L. R.; Love, J. A. J. Am. Chem. Soc. 2005, 127, 17614–17615; (e) Kondoh, A.;
Takami, K.; Yorimitsu, H.; Oshima, K. J. Org. Chem. 2005, 70, 6468–6473; (f)
Brouwer, C.; Rahaman, R.; He, C. Synlett 2007, 1785–1789; (g) Yadav, J. S.; Reddy,
B. V. S.; Ravindar, A. R. K.; Baishy, G. Chem. Lett. 2007, 36, 1474–1475; (h) Weiss, C.
J.; Wobser, S. D.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 2062–2063.
7. (a) Ogawa, A.; Kawakami, J.; Sonoda, N.; Hirau, T. J. Org. Chem. 1996, 61, 4161–
4163; (b) Kodama, S.; Nomoto, A.; Kajitani, M.; Nishinaka, E.; Sonoda, M.;
Ogawa, A. J. Sulfur Chem. 2009, 30, 309–318.
8. Morita, N.; Krause, N. Angew. Chem., Int. Ed. 2006, 45, 1894–1899.
9. (a) Nishina, N.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3314–3317; (b)
Nishina, N.; Yamamoto, Y. Synlett 2007, 1767–1770; (c) Nishina, N.; Yamamoto,
Y. Tetrahedron Lett. 2008, 49, 4908–4911; (d) Nishina, N.; Yamamoto, Y.
Tetrahedron 2009, 65, 1799–1808.
63.5, 48.3, 27.7, 21.3; IR (neat) 1590, 1473, 1080, 881, 853, 789, 751, 694 cmꢀ1
HRMS (ESI) Calcd for C23H24S2Na (M+Na) 387.1212. Found 387.1211.
;
Compound 3h: White solid; mp 112 °C; 1H NMR (CDCl3, 400 MHz) d 7.20–7.50
(m, 13H), 3.12 (s, 2H), 1.25 (s, 3H); 13C NMR (CDCl3, 100 MHz) d 138.1, 135.8,
131.7, 131.1, 130.9, 127.8, 127.0, 123.9, 63.9, 48.2, 27.6; IR (neat) 1580, 1471,
1435, 1303, 1062, 1022, 746, 702, 690 cmꢀ1; HRMS (ESI) Calcd for C21H18Br2S2Na
(M+Na) 514.9109. Found 514.9108.
Compound 3i: Colorless oil; 1H NMR (CDCl3, 400 MHz) d 7.55–7.60 (m, 2H), 7.47–
7.53 (m, 2H), 7.35–7.40 (m, 2H), 7.20–7.35 (m, 7H), 3.17 (s, 2H), 1.30 (s, 3H); 13
C
NMR (CDCl3, 100 MHz) d 136.1, 135.7, 134.7, 134.1, 133.7, 131.1, 129.6, 129.3,
127.8, 127.0, 64.3, 48.4, 27.7; IR (neat) 1573, 1561, 1459, 1070, 881, 776, 700,
680 cmꢀ1
427.0118.
; HRMS (ESI) Calcd for C21H18Cl2S2Na (M+Na) 427.0119. Found
10. The E/Z isomers of 4a were identified by comparison with the literature, see:
Silveira, C. C.; Perin, G.; Braga, A. L.; Dabdoub, M. J.; Jacob, R. G. Tetrahedron
1999, 55, 7421–7432.