P.N. Chatterjee, S. Roy / Tetrahedron 68 (2012) 3776e3785
3785
Podder, S.; Choudhury, J.; Roy, S. J. Org. Chem. 2007, 72, 3100; (g) Roy, U. K.; Roy,
S. Chem. Rev. 2010, 110, 2472 and references therein.
129.2, 129.9, 130.1, 133.1, 133.4, 135.0, 139.2. DEPT 135:
22.7, 33.8, 51.5, 127.7, 128.8, 128.9, 129.2, 129.9, 130.1. CHN: Anal.
Calcd. for (C18H18Cl2S), C: 64.09, H: 5.38; found, C: 64.53, H: 5.11.
d ppm 13.6,
7. Wang, J.;Huang, W.;Zhang, Z.;Xiang, X.;Liu, R.; Zhou, X.J.Org.Chem.2009, 74, 3299.
8. Fitzpatrick, P. F.; Flory, D. R., Jr.; Villafranca, J. J. Biochemistry 1985, 24, 2108.
9. (a)Nishibayashi, Y.; Yamanashi, M.; Takagi, Y.; Hidai, M. Chem. Commun.1997, 859;
(b) Onodera, G.; Imajima, H.; Yamanashi, M.; Nishibayashi, Y.; Hidai, M.; Uemura,
S. Organometallics 2004, 23, 5841; (c) Hubert, C.; Renaud, J.; Demerseman, B.;
Fischmeister, C.; Bruneau, C. J. Mol. Catal. A: Chem. 2005, 237,161; (d) Zaitsev, A. B.;
Caldwell, H. F.; Pregosin, P. S.; Veiros, L. F. Chem.dEur. J. 2009, 15, 6468.
10. (a) Polet, D.; Rathgeb, X.; Faiciola, C. A.; Langlois, J.; Hajjajji, S. E.; Alexakis, A.
Chem.dEur. J. 2009, 15, 1205; (b) Xu, Q.; Liu, W.; Dai, L.; You, S. J. Org. Chem.
2010, 75, 4615 and the references therein.
4.4.16. (E)-2-(1,3-Bis(4-chlorophenyl)allylthio)ethanol (6d). 1H NMR
(CDCl3, 200 MHz): d ppm 2.32 (s,1H), 2.58e2.76 (m, 2H), 3.72 (t, 2H,
J¼6.0 Hz), 4.63 (d, 1H, J¼8.0 Hz), 6.24e6.35 (dd, 1H, J¼8.0, 15.8 Hz),
6.44 (d, 1H, J¼15.8 Hz), 7.23e7.38 (m, 8H). 13C NMR (CDCl3,
54.6 MHz):
d ppm 34.7, 51.3, 60.9, 127.8, 128.8, 129.0, 129.2, 129.5,
130.5, 133.4, 133.6, 134.7, 138.7. DEPT 135:
127.8, 128.8, 129.0, 129.2, 129.5, 130.5. CHN: Anal. Calcd. for
(C17H16Cl2OS), C: 60.18, H: 4.75; found, C: 60.02, H: 4.86.
d ppm 34.7, 51.3, 60.9,
11. Yatsumonji, Y.; Ishida, Y.; Tsubouchi, A.; Takeda, T. Org. Lett. 2007, 9, 4603.
12. Yang, H.; Fang, L.; Zhang, M.; Zhhu, C. Eur. J. Org. Chem. 2009, 666.
13. (a) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M.
J. Am. Chem. Soc. 2002, 124,10968; (b) Manabe, K.; Kobayashi, S. Org. Lett. 2003, 5,
3241; (c) Kayaki, Y.; Koda, T.; Ikariya, T. J. Org. Chem. 2004, 69, 2595; (d) Tsuka-
moto, H.; Sato, M.; Kondo, Y. Chem. Commun. 2004, 1200; (e) Kimura, M.; Futa-
mata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592; (f) Yang, S.-C.;
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rahedron 2008, 64, 1204; (i) Usui, I.; Schmidt, S.; Breit, B. Org. Lett. 2009, 11, 1453.
14. Yadav, J. S.; Reddy, B. V. S.; Rao, T. S.; Rao, K. V. R. Tetrahedron Lett. 2008, 49, 614.
15. A few selected recent references: Ag-catalyst: (a) Bandini, M.; Eichholzer, A.;
Kotrusz, P.; Tragni, M.; Troisi, S.; Umani-Ronchi, A. Adv. Synth. Catal. 2009, 351,
319 Au-catalyzed; (b) Guo, S.; Song, F.; Liu, Y. Synlett 2007, 964; (c) Rao, W.;
Chan, P. W. H. Org. Biomol. Chem. 2008, 6, 2426 In-catalyzed; (d) Yasuda, M.;
Somyo, T.; Baba, A. Angew. Chem., Int. Ed. 2006, 45, 793; (e) Krishna, P. R.; Se-
khar, E. R.; Prapurna, Y. L. Tetrahedron Lett. 2007, 48, 9048; (f) Yadav, J. S.; Reddy,
B. V. S.; Aravind, S.; Kumar, G. G. K. S. N.; Reddy, A. S. Tetrahedron Lett. 2007, 48,
6117 Fe-catalyzed; (g) Jana, U.; Maiti, S.; Biswas, S. Tetrahedron Lett. 2007, 48,
7160; (h) Jana, U.; Maiti, S.; Biswas, S. Tetrahedron Lett. 2007, 48, 4065 Sc(OTf)3-
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1997, 62, 6997 Yb(OTf)3-catalyzed; (j) Huang, W.; Wang, J.; Shen, Q.; Zhou, X.
Tetrahedron Lett. 2007, 48, 3969; (k) Huang, W.; Wang, J.; Shen, Q.; Zhou, X.
Tetrahedron 2007, 63, 11636 Bi(OTf)3-catalyzed; (l) Qin, H.; Yamagiwa, N.;
Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2007, 46, 409; (m) Rueping,
M.; Nachtsheim, B. J.; Kuenkel, A. Org. Lett. 2007, 9, 825 Other metal triflates-
catalyzed; (n) Noji, M.; Konno, Y.; Ishii, K. J. Org. Chem. 2007, 72, 5161.
16. A few selected recent references: Brønsted acid-catalyzed: (a) Espeel, P. H.;
Janssens, B.; Jacobs, P. A. J. Org. Chem. 1993, 58, 7688; (b) Smith, K.; Pollaud, G.
M. J. Chem. Soc., Perkin Trans. 1 1994, 3519; (c) Smith, K.; Pollaud, G. M.; Mat-
thews, I. Green Chem. 1999, 75; (d) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron
Lett. 1997, 38, 2521; (e) Motokura, K.; Fujita, N.; Mori, K.; Mizugaki, T.; Ebitani,
K.; Kaneda, K. Angew. Chem., Int. Ed. 2006, 45, 2605; (f) Liu, P. N.; Zhou, Z. Y.; Lau,
C. P. Chem.dEur. J. 2007, 13, 8610; (g) Shirakawa, S.; Kobayashi, S. Org. Lett. 2007,
9, 311; (h) Motokura, K.; Nakagiri, N.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Org.
Chem. 2007, 72, 6006; (i) Bras, J. L.; Muzart, J. Tetrahedron 2007, 63, 7942; (j)
Wang, G.; Shen, Y.; Wu, X. Eur. J. Org. Chem. 2008, 4367; (k) Reddy, C. R.; Sri-
kanth, B.; Rao, N. N.; Shin, D. Tetrahedron 2008, 64, 11666; (l) Yadav, J. S.; Reddy,
B. V. S.; Pandurangam, T.; Rao, K. V. R.; Praneeth, K.; Kumar, G. G. K. S. N.;
Madavi, C.; Kunwar, A. C. Tetrahedron Lett. 2008, 49, 4296 A recent review on
Brønsted or Lewis acids catalyzed direct substitution of allylic, benzylic and
propargylic alcohol; (m) Emer, E.; Sinisi, R.; Capdevila, M. G.; Petruzziello, D.;
Vincentiis, F. D.; Cozzi, P. G. Eur. J. Org. Chem. 2011, 647.
4.4.17. (E)-4,40-(3-Ethoxyprop-1-ene-1,3-diyl)bis(chlorobenzene)
(7a). 1H NMR (CDCl3, 200 MHz):
d
ppm 1.27 (t, 3H, J¼7.2 Hz), 3.52
(q, 2H, J¼7.2 Hz), 4.89 (d, 1H, J¼6.8 Hz), 6.18e6.29 (dd, 1H, J¼6.8,
15.8 Hz), 6.56 (d, 1H, J¼15.8 Hz), 7.12e7.45 (m, 8H). 13C NMR (CDCl3,
54.6 MHz):
d ppm 15.4, 64.2, 81.7, 127.8, 128.2, 128.7, 130.2, 130.9,
133.5, 135.0, 139.9. DEPT 135:
d ppm 15.4, 64.2, 81.7, 127.8, 128.2,
128.7, 130.2, 130.9. CHN: Anal. Calcd. for (C17H16Cl2O), C: 66.46, H:
5.25; found, C: 66.59, H: 5.38.
4.4.18. (E)-4,40-(3-Isopropoxyprop-1-ene-1,3-diyl)bis(-
bromobenzene) (7b). 1H NMR (CDCl3, 200 MHz):
d ppm 1.15 (d, 3H,
J¼6.2 Hz), 1.20 (d, 3H, J¼6.2 Hz), 3.60e3.72 (m, 1H), 4.96 (d, 1H,
J¼6.6 Hz), 6.15e6.26 (dd, 1H, J¼6.6, 15.8 Hz), 6.47 (d, 1H, J¼15.8 Hz),
7.19 (d, 2H, J¼8.6 Hz), 7.24 (d, 2H, J¼8.2 Hz), 7.38 (d, 2H, J¼8.6 Hz), 7.46
(d, 2H, J¼8.2 Hz). 13C NMR (CDCl3, 54.6 MHz):
d ppm 22.2, 22.5, 69.1,
78.7, 121.4, 121.5, 128.1, 128.6, 129.8, 131.6, 135.5, 140.8. CHN: Anal.
Calcd. for (C18H18Br2O), C: 52.17, H: 4.42; found, C: 52.85, H: 4.20.
4.4.19. (E)-4,40-(3-(Benzyloxy)prop-1-ene-1,3-diyl)bis(-
bromobenzene) (7c). 1H NMR (CDCl3, 200 MHz):
d ppm 4.58 (s, 2H),
4.98 (d,1H, J¼6.6 Hz), 6.24e6.35 (dd,1H, J¼6.6,15.8 Hz), 6.58 (d,1H,
J¼15.8 Hz), 7.23e7.56 (m, 13H). 13C NMR (CDCl3, 54.6 MHz):
d ppm
70.4, 80.8, 121.8, 127.8, 128.2, 128.5, 128.7, 130.6, 131.8, 135.4, 138.1,
139.9. DEPT 135:
d ppm 70.4, 80.8, 127.8, 128.2, 128.5, 128.7, 130.6,
131.8. CHN: Anal. Calcd. for (C22H18Br2O), C: 57.67, H: 3.96; found, C:
57.41, H: 4.02.
Acknowledgements
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We thank DST (financial support to S.R.), and CSIR (fellowship to
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and many help.
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