Chemistry Reference
In-Depth Information
an electron-donating methyl group (R
Me) reacted 14.3 times faster than the corresponding ester (R
=
CO
2
Me). The pyridylsulfonyl group could be removed under mildly reducing conditions to give the vinylated
pyrrole
3.187
; more strongly reducing conditions also reduced the alkene, to give the alkyl pyrrole
3.188
.
In the indole series, the
N
-pyridylsulfonyl indole
3.189
gave the product of C2 vinylation
3.190
, rather
than the typical C3 vinylation, showing that the coordination effect of the pyridine can overwhelm the normal
indole reactivity (Scheme 3.74). The reaction presumably proceeds via a chelated palladium intermediate
3.192
.
75
Interestingly, an indole dimer
3.191
is produced in the absence of an added alkene, showing that the
palladium(II) intermediate is capable of attacking a second molecule of the substrate.
=
References
1. (a) Godula, K.; Sames, D.
Science
2006
,
312
, 67; (b) Alberico, D.; Scott, M. E.; Lautens, M.
Chem. Rev.
2007
,
107
,
174; (c) Campeau, L.-C.; Stuart, R.; Fagnou, K.
Aldrich. Acta
2007
,
40
, 35; (d) Seregin, I. V.; Gevorgyan, V.
Chem.
Soc. Rev.
2007
,
36
, 1173; (e) Colby, D. A.; Bergman, R. G.; Ellman, J. A.
Chem. Rev.
2009
,
110
, 624; (f) Jazzar, R.;
Hitce, J.
et al. Chem. Eur. J.
2010
,
16
, 2654; (g) McMurray, L.; O'Hara, F.; Gaunt, M. J.
Chem. Soc. Rev.
2011
,
40
,
1885; (h) Baudoin, O.
Chem. Soc. Rev.
2011
,
40
, 4902.
2. Robinson, N. P.; Main, L.; Nicholson, B. K.
J. Organomet. Chem.
1988
,
349
, 209.
3. Depree, G. L.; Main, L.
et al. J. Organomet. Chem.
2006
,
691
, 667.
4. Le Bras, J.; Muzart, J.
Chem. Rev.
2011
,
111
, 1170.
5. Dams, M.; De Vos, D. E.
et al. Angew. Chem., Int. Ed.
2003
,
42
, 3512.
6. Wang, D.-H.; Engle, K. M.
et al. Science
2010
,
327
, 315.
7. Tsuji, J.; Nagashima, H.
Tetrahedron
1984
,
40
, 2699.
8. Grimster, N. P.; Gauntlett, C.
et al. Angew. Chem., Int. Ed.
2005
,
44
, 3125.
9. Houlden, C. E.; Bailey, C. D.
J. Am. Chem. Soc.
2008
,
130
, 10066.
10. Trost, B. M.; Godleski, S. A.; Genet, J. P.
J. Am. Chem. Soc.
1978
,
100
, 3930.
11. Ferreira, E. M.; Stoltz, B. M.
J. Am. Chem. Soc.
2003
,
125
, 9578.
12. Liu, C.; Han, X.
etal.J.Am.Chem.Soc.
2004
,
126
, 3700.
13. Hostyn, S.; Tehrani, K. A.
et al. Tetrahedron
2011
,
67
, 655.
14. Brenner, M.; Mayer, G.
et al. Chem. Eur. J.
1997
,
3
, 70.
15. Shelbu, Q.; Kataoka, N.
et al. J. Am. Chem. Soc.
2000
,
122
, 10718.
16. LeBlanc, M.; Fagnou, K.
Org. Lett.
2005
,
7
, 2849.
17. Bowie, A. L.; Trauner, D.
J. Org. Chem.
2009
,
74
, 1581. For early work by the same group in a synthesis of
Rhazinilam, see Bowie, A. L.; Hughes, C. C.; Trauner, D.
Org. Lett.
2005
,
7
, 5207.
18. Niphakis, M. J.; Georg, G. I.
J. Org. Chem.
2010
,
75
, 6019.
19. Berman, A. M.; Bergman, R. G.; Ellman, J. A.
J. Org. Chem.
2010
,
75
, 7863.
20. Lewis, C. J.; Bergman, R. G.; Ellman, J. A.
J. Am. Chem. Soc.
2007
,
129
, 5332.
21. Ding, Z.; Yoshikai, N.
Org. Lett.
2011
,
12
, 4180.
22. Yoshikai, N.
Synlett
2011
, 1047.
23. Chatani, N.; Fukuyama, T.
et al. J. Am. Chem. Soc.
1996
,
118
, 493.
24. Han, W.; Ofial, A. R.
Synlett
2011
, 1951.
25. Xi, P.; Yang, F.
et al. J. Am. Chem. Soc.
2010
,
132
, 1822.
26. Wang, X.; Leow, D.; Yu, J.-Q.
J. Am. Chem. Soc.
2011
,
133
, 13864.
27. Willis, M. C.
Chem. Rev.
2010
,
110
, 725.
28. (a) Lochow, C. F.; Miller, R. G.
J. Am. Chem. Soc.
1976
,
98
, 1281; (b) Gable, K. P.; Benz, G. A.
Tetrahedron Lett.
1991
,
32
, 3473.
29. Fairlie, D. P.; Bosnich, B.
Organometallics
1988
,
7
, 936.
30. Vinogradov, M. G.; Tuzikov, A. B.
et al. J. Organomet. Chem.
1988
,
348
, 123.
31. Barnhart, R. W.; McMorran, D. A.; Bosnich, B.
Chem. Commun.
1997
, 589.
32. Aloise, A. D.; Layton, M. E.; Shair, M. D.
J. Am. Chem. Soc.
2000
,
122
, 12610.
