7994
B.R. Buckley, S.P. Neary / Tetrahedron 66 (2010) 7988e7994
Wiley-VCH: New York, NY, 1998; (j) Link, J. T.; Overman, L. E. Chemtech 1998,
4.9.6. n-Butyl-trans-cinnamate29
.
nmax (film)/cmꢂ1 3061, 3028,
28, 19; (k) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447; (l)
Reetz, M. T. In Transition Metal Catalyzed Reactions; Davies, S. G., Murahashi,
S.-I., Eds.; Blackwell Sci.: Oxford, 1999.
6. (a) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10; (b) Littke, A. F.; Fu, G. C. J. Am.
Chem. Soc. 2001, 123, 6989; (c) Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am.
Chem. Soc. 1999, 121, 2123; (d) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.;
Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2677; (e) Ehrentraut, A.; Zapf, A.; Beller,
M. Synlett 2000, 1589.
7. (a) Ben-David, Y.; Portnoy, M.; Gozin, M.; Milstein, D. Organometallics 1992, 11,
1995; (b) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1655; (c) Portnoy,
M.; Ben-David, Y.; Milstein, D. Organometallics 1993, 12, 4734; (d) Portnoy, M.;
Ben-Dvid, Y.; Rousso, I.; Milstein, D. Organometallics 1994, 13, 3465; (e) Shaw, B.
L.; Perera, S. D. Chem. Commun. 1998, 1863.
8. For recent reviews on palladacycles for Heck reactions, see: (a) Dupont, J.;
Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917; (b) Benford, R. B. Chem.
Commun. 2003, 1787.
2959, 2933, 2873, 1713, 1638, 1449, 1310, 1280, 1172, 980, 768, 699;
1H NMR (400 MHz, CDCl3) 0.84 (3H, t, J¼7 Hz), 1.27e1.38 (2H, m),
1.55e1.62 (2H, m), 4.1 (2H, t, J¼7 Hz), 6.31 (1H, d, J¼16 Hz),
7.24e7.28 (3H, m), 7.37e7.43 (2H, m), 7.6 (1H, d, J¼16 Hz); 13C NMR
(100 MHz, CDCl3) 13.7, 19.1, 30.6, 64.0, 117.5, 128.4, 129.0, 130.3,
134.5, 144.5, 166.2.
4.9.7. trans-4-Chlorostilbene31. nmax (film)/cmꢂ1 3079, 3019,
2919, 1591, 1448, 1405, 1112, 966, 817, 751, 690; 1H NMR
(400 MHz CDCl3) 7.06 (2H, d, J¼3 Hz), 7.25e7.40 (5H, m), 7.44
(2H, d, J¼9 Hz), 7.51 (2H, d, J¼7.2 Hz); 13C NMR (100 MHz,
CDCl3) 126.5, 127.4, 127.7, 127.9, 128.7, 128.9, 129.3, 133.2, 135.8,
136.9.
9. For the use of tetraphenylphosphonium salts in Heck reactions, see: Reetz, M.
T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. 1998, 37, 481.
10. Phosphine oxidation is a noted problem in bioconjugation Laughlin, S. T.;
Bertozzi, C. R. Nat. Protoc. 2007, 2, 2930.
4.9.8. 1-Fluoro-3-[(E)-2-(4-methoxyphenyl)vinyl]benzene32
. nmax
(film)/cmꢂ1 2932, 1600, 1508, 1489, 1232, 1098, 968, 834; 1H
NMR (400 MHz CDCl3) 3.84 (3H, s), 6.84e6.96 (4H, m), 7.03 (2H,
t, J¼9 Hz), 7.41e7.47 (4H, m); 13C NMR (100 MHz, CDCl3) 115.6,
115.8, 127.6, 128.0, 128.1, 128.9, 133.2, 135.6, 161.2, 163.7.
11. (a) Arduengo, A. J. Acc. Chem. Res. 1999, 32, 913; (b) Herrmann, W. A.; Goossen,
€
L. J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805; (c)
€
Herrmann, W. A.; Goossen, L. J.; Artus, G. R. J.; Kocher, C. Organometallics 1997,
16, 2472; (d) Seiders, J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225; (e)
Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951; (f) Page, P. C. B.;
Buckley, B. R.; Christie, S. D. R.; Edgar, M.; Poulton, A. M.; Elsegood, M. R. J.;
McKee, V. J. Organomet. Chem. 2005, 690, 6210.
4.9.9. 1-Chloro-3-[(E)-2-(4-methoxyphenyl)vinyl]benzene30
. nmax
12. Yang, D.; Chen, Y.-C.; Zhu, N.-Y. Org. Lett. 2004, 6, 1577.
13. (a) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297; (b) Miao, H.; Yang, Z. Org.
(film)/cmꢂ1 2924, 2843, 1605, 1512, 1489, 1254, 1111, 1032, 832,
737, 615; 1H NMR (400 MHz CDCl3) 3.84 (3H, s), 6.87e6.94 (2H,
m), 7.03 (2H, d, J¼13 Hz), 7.31 (2H, d, J¼12 Hz), 7.43 (4H, m); 13C
NMR (100 MHz, CDCl3) 55.3, 114.2, 125.6, 127.4, 127.8, 128.8,
130.2, 132.7, 136.2, 159.5.
Lett. 2000, 2, 1765; (c) Hu, Y.; Yang, Z. Org. Lett. 2001, 3, 1387.
14. (a) Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem.
2001, 634, 39; (b) Masllorens, J.; Moreno-Mañas, M.; Pla-Quintana, A.; Roglans,
A. Org. Lett. 2003, 5, 1559; (c) Masllorens, J.; Roglans, A. Organomet. 2004, 23,
2533; (d) Chalker, J. M.; Wood, C. S. C.; Davies, B. G. J. Am. Chem. Soc. 2009, 131,
16346.
15. (a) Hultén, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide,
4.9.10. 1-Methoxy-3-[(E)-2-(4-methylphenyl)vinyl]benzene29
.
nmax
€
A.; Åqvist, J.; Classon, B.; Danielson, U. H.; Karlén, A.; Kvarnstrom, I.; Sa-
(film)/cmꢂ1 3020, 2935, 2837, 1605, 1512, 1462, 1250, 1177, 1110,
1032, 968, 828, 737; 1H NMR (400 MHz CDCl3) 2.28 (3H, s), 3.75
(3H, s), 6.82 (2H, d, J¼9 Hz), 6.87 (1H, d, J¼16 Hz), 6.95 (1H, d,
J¼16 Hz), 7.07 (2H, d, J¼8 Hz), 7.31 (2H, d, J¼8 Hz), 7.37 (2H, d,
J¼8 Hz); 13C NMR (100 MHz, CDCl3) 21.2, 55.3, 114.1, 126.2, 126.6,
127.2, 127.6, 129.4, 130.4, 134.9, 137.1, 159.2.
€
€
muelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885; (b) Backbro, K.; Lowgren,
S.; Österlund, K.; Atepo, J.; Unge, T.; Hultén, J.; Bonham, N. M.; Schaal, W.;
Karlén, A.; Hallberg, A. J. Med. Chem. 1997, 40, 898.
16. Castro, J. L.; Matassa, V. G.; Ball, R. G. J. Org. Chem. 1994, 59, 2289.
17. (a) Ahn, K.-H.; Yoo, D.-J.; Kim, J.-S. Tetrahedron Lett. 1992, 33, 6661; (b) Pansare,
S. V.; Rai, A. N.; Kate, S. N. Synlett 1998, 623; (c) Sartor, D.; Saffrich, J.; Helmchen,
G.; Richards, C. J.; Lambert, H. Tetrahedron: Asymmetry 1991, 2, 639; (d) Op-
polzer, W.; Starkemann, C.; Rodriguez, I.; Bernadinelli, G. Tetrahedron Lett. 1991,
32, 61; (e) Oppolzer, W.; Kingma, A. J.; Pillai, S. K. Tetrahedron Lett. 1991, 32,
4893; Richey, H. G., Jr.; Farkas, J., Jr. J. Org. Chem. 1987, 52, 479.
18. Richey, H. G., Jr.; Farkas, J., Jr. J. Org. Chem. 1987, 52, 479.
Acknowledgements
19. (a) Dewynter, G.; Ubaldi, S.; Voyer, N.; Toupet, L. Tetrahedron Lett. 1998, 39,
7434; (b) Boudjabi, S.; Dewynter, G.; Voyer, N.; Toupet, L. Eur. J. Org. Chem. 1999,
9, 2275; (c) Regainia, Z.; Abdaoui, M.; Aouf, N. E.; Dewynter, G.; Montero, J. L.
Tetrahedron 2000, 56, 381.
20. Buckley, B. R.; Neary, S. P. Adv. Synth. Catal. 2009, 351, 71.
21. Using a Biotage Initiator Eight EXP Microwave System.
The authors would like to thank Loughborough University for
funding a Ph.D. studentship (SPN) and Research Councils UK for
a RCUK fellowship (BRB).
22. Initially when the Pd2(dba)3-ligand solutions were prepared they took on
a dark red colour. After sufficient stirring they gradually changed to a bright
yellow, indicating generation of the active form. When making larger stock
solutions we observed that the activation times could be significantly longer
with significant amounts of palladium black precipitating in the process. We
later found that the activation times were improved by exposing as much of the
surface area of the solution as possible to air while stirring vigorously. The
palladium black can simply be filtered from the solution or allowed to settle to
the bottom of the container, while the solution is taken from the surface. We
later discovered that by doubling the number of equivalents of ligand, the
palladium black precipitate was eliminated from the stock solution.
23. Katritzky, A. R.; Fan, J.; Fu, C. J. Org. Chem. 1990, 55 (10), 3209.
24. (a) Amatore, C.; Jutland, A. Acc. Chem. Res. 2000, 33, 314; (b) Amatore, C.; Carré,
E.; Jutland, A.; Medjour, Y. Organometallics 2002, 21, 4540.
Supplementary data
Supplementary data associated with this article can be found in
References and notes
1. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
2. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61 (50), 11771.
3. (a) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581; (b) Heck,
R. F.; Nolly, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
4. (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146; (b) De Meijere, A.; Meyer, F. E.
Angew. Chem., Int. Ed. Engl. 1995, 33, 2379; (c) Cabri, W.; Candiani, I. Acc. Chem.
Res. 1995, 28, 2; (d) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.; Liu, F. Chem. Rev.
1996, 96, 365; (e) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427; (f) Whitcombe, N. J.;
Kuok Hii, K.; Gibson, S. E. Tetrahedron 2001, 57, 7449; (g) Dounay, A. B.; Over-
man, L. E. Chem. Rev. 2003, 103, 2945.
25. Amatore, C.; Carré, E.; Jutland, A.; Shaik, S. Organometallics 2002, 21, 2319.
26. Henriksen, S. T.; Norrby, P. O.; Kaukoranta, P.; Andersson, P. G. J. Am. Chem. Soc.
2008, 130, 10414 and references cited therein.
27. Reetz, M. T.; Westermann, E.; Lohmer, R.; Lohmer, G. Tetrahedron Lett. 1998,
8449.
28. Willans, C. E.; Mulders, J. M. C. A.; de Vries, J. G.; de Vries, A. H. M. J. Organomet.
Chem. 2003, 687, 494.
29. Kantam, M. L.; Srinivas, P.; Yadav, J.; Likhar, P. R.; Bhargava, S. J. Org. Chem. 2009,
74, 4882.
30. Pruka1a, W.; Majchrzak, M.; Pietraszuk, C.; Marciniec, B. J. Mol. Catal. A: Chem.
2006, 254, 58.
31. Luo, F.; Pan, C.; Wang, W.; Ye, Z.; Cheng, J. Tetrahedron 2010, 66, 1399.
32. Shi, M.; Xu, B. J. Org. Chem. 2002, 67, 294.
33. Douglas, R. A.; Crabtree, R. H. Organometallics 1983, 2, 855.
34. (a) Fairlamb, I. J. S. Org. Biomol. Chem. 2008, 6, 3645; (b) Fairlamb, I. J. S.; Kapdi,
A. R.; Lee, A. F.; McGlacken, G. P.; Weissburger, F.; de Vries, A. H. M.; Schmieder-
van de Vondervoort, L. Chem.dEur. J. 2006, 12, 8750.
5. For useful reviews covering different aspects of Heck chemistry see for ex-
ample: (a) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.,
Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4; (b) Heck, R. F. Org. React.
(N.Y.) 1982, 27, 345; (c) Daves, G. D.; Hallberg, A. Chem. Rev. 1989, 89, 1433;
(d) De Meijere, A.; Braese, S. In Transition Metal Catalyzed Reactions; Davies,
S. G., Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (e) Jeffery, T. In
Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; Jai: Greenwich,
CT, 1996; Vol. 5; (f) Brase, S.; De Meijere, A. In Metal-Catalyzed Cross-Coupling
Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, NY, 1998;
Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371; (h)
Overman, L. E. Pure Appl. Chem. 1994, 66, 1423; (i) Link, J. T.; Overman, L. E.
In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.;