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M. Feuerstein et al.
SPECIAL TOPIC
(11) Ohff, M.; Ohff, A.; van der Boom, M.; Milstein, D. J. Am.
Chem. Soc. 1997, 119, 11687.
(12) Miyaazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron
Lett. 1999, 40, 7379.
(13) (a) For examples of Suzuki or Heck reaction using SCS type
ligands: Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem.
Soc. 1999, 121, 9531. (b) See also Ref.5a
References
(1) For reviews on palladium catalysis: (a) Tsuji, J. Palladium
Reagent and Catalysis, Innovation in Organic Synthesis;
Wiley: New York, 1995. (b) Malleron, J.-L.; Fiaud, J.-C.;
Legros, J.-Y. Handbook of Palladium Catalyzed Organic
Reaction; Academic Press: London, 1997.
(2) For reviews on allylic substitution reactions: (a)Hayashi,T.
In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH:
New York, 1993, 325. (b) Pfaltz, A.; Lautens, M.
Comprehensive Asymmetric Catalysis II; Jacobsen, E. N.;
Pfaltz, A.; Yamamoto, H., Eds.; Springer Verlag:
Heidelberg, 1999, 833. (c) Consiglio, G.; Waymouth, R. M.
Chem. Rev. 1989, 89, 257.
(3) For a review on the cross coupling of aryl bromides with
arylboronic acids: Suzuki, A. Metal-Catalysed Cross-
Coupling Reaction; Diederich, F.; Stang, P. J., Eds.; Wiley:
New York, 1998.
(4) For reviews on the palladium-catalyzed Heck reaction:
(a) Heck, R. F. Vinyl Substitution with Organopalladium
Intermediates, In Comprehensive Organic Synthesis, Vol. 4;
Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991.
(b) Reetz, M. T. Transition Metal Catalyzed Reactions;
Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell: Oxford,
1999. (c) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000,
100, 3009.
(5) (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.;
Brossmer, C. Angew. Chem. Int. Ed. Engl. 1995, 34, 1848.
(b) Herrmann, W.; Brossmer, C.; Reisinger, C.-P.; Reimeier,
T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357.
(c) Herrmann, W. A.; Bohm, V. P. C.; Reisinger, C.-P. J.
Organomet. Chem. 1999, 576, 23.
(14) (a) Wolfe, J.; Buchwald, S. Angew. Chem. Int. Ed. 1999, 38,
2413. (b) Wolfe, J.; Singer, R.; Yang, B.; Buchwald, S. J.
Am. Chem. Soc. 1999, 121, 9550. (c) Old, D.; Wolfe, J.;
Buchwald, S. J. Am. Chem. Soc. 1998, 120, 9722. (d) Bei,
X.; Turner, H.; Weinberg, H.; Guram, A. J. Org. Chem.
1999, 64, 6797. (e) Littke, A.; Fu, G. J. Org. Chem. 1999,
64, 10. (f) Littke, A.; Dai, C.; Fu, G. J. Am. Chem. Soc. 2000,
122, 4020. (g) Zapf, A.; Ehrentraut, A.; Beller, M. Angew.
Chem. Int. Ed. 2000, 39, 4153.
(15) For examples of Suzuki cross-coupling using carbene
ligands: (a) Weskamp, T.; Böhm, V. P. W.; Herrmann, W.
A. J. Organomet. Chem. 1999, 585, 348. (b) Zhang, C.;
Huang, J.; Trudell, M.; Nolan, S. J. Org. Chem. 1999, 64,
3804. (c) Böhm, V. P. W.; Gstöttmayr, C.; Weskamp, T.;
Herrmann, W. A. J. Organomet. Chem. 2000, 595, 186.
(d) Zhang, C.; Trudell, M. Tetrahedron Lett. 2000, 41, 595.
(e) McGuiness, D.; Cavell, K. Organometallics 2000, 19,
741.
(16) (a) Mason, M. R.; Duff, C. M.; Miller, L. L.; Jacobson, R.
A.; Verkade, J. G. Inorg. Chem. 1992, 31, 2746.
(b) Steenwinkel, P.; Kolmschott, S.; Gossage, R. A.; Dani,
P.; Veldman, N.; Speck, A. L.; van Koten, G. Eur. J. Inorg.
Chem. 1998, 477. (c) Bianchini, C.; Lee, H. M.; Meli, A.;
Oberhauser, W.; Vizza, F.; Brüggeller, P.; Haid, R.; Langes,
C. Chem. Commun. 2000, 777.
(17) For a review on the synthesis of polypodal
diphenylphosphine ligands: Laurenti, D.; Santelli, M. Org.
Prep. Proc. Int. 1999, 31, 245.
(18) Laurenti, D.; Feuerstein, M.; Pèpe, G.; Doucet, H.; Santelli,
M. J. Org. Chem. 2001, 66, 1633.
(19) Feuerstein, M.; Laurenti, D.; Doucet, H.; Santelli, M. Chem.
Commun. 2001, 43.
(20) For a review on palladium-catalyzed reactions in aqueous
medium: Genet, J.-P.; Savignac, M. J. Organomet. Chem.
1999, 576, 305.
(21) Feuerstein, M.; Laurenti, D.; Doucet, H.; Santelli, M.
Tetrahedron Lett. 2001, 42, 2313.
(22) For a review on biaryl synthesis: Stanforth, S. Tetrahedron
1998, 54, 263.
(23) Feuerstein, M.; Laurenti, D.; Bougeant, C.; Doucet, H.;
Santelli, M. Chem. Commun. 2001, 325.
(24) (a) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M.; Mottier,
L. Organometallics 1993, 12, 3168. (b) Amatore, C.;
Broeker, G.; Jutand, A.; Khalil, F. J. Am. Chem. Soc. 1997,
119, 5176. (c) Amatore, C.; Jutand, A. Acc. Chem. Res.
2000, 33, 314.
(25) Padwa, A.; Filipkowski, M. A.; Meske, M.; Murphree, S.;
Watterson, S. H.; Ni, Z. J. Org. Chem. 1994, 59, 588.
(26) Bergbreiter, D. E.; Liu, Y.; Osburn, P. J. Am. Chem. Soc.
1998, 120, 4250.
(6) Gibson, S.; Foster, D.; Eastham, G.; Tooze, R.; Cole-
Hamilton, D. Chem. Commun. 2001, 779.
(7) For examples of Suzuki or Heck reactions using phosphite
ligands: (a) Bedford, R.; Welch, S. Chem. Commun. 2001,
129. (b) Albisson, D.; Bedford, R.; Scully, N. Tetrahedron
Lett. 1998, 39, 9793. (c) Zapf, A.; Beller, M. Chem. Eur. J.
2000, 6, 1830. (d) Zapf, A.; Beller, M. Synlett 1998, 792.
(8) For examples of Suzuki or Heck reactions using amine
ligands: (a) Weissman, H.; Milstein, D. Chem. Commun.
1999, 1901. (b) Ohff, M.; Ohff, A.; Milstein, D. Chem.
Commun. 1999, 357. (c) Iyer, S.; Ramesh, C. Tetrahedron
Lett. 2000, 41, 8981. (d) Alonso, D. A.; Najera, C.; Pacheco,
M. C. Org. Lett. 2000, 2, 1823. (e) Beletskaya, I.; Kashin,
A.; Karlstedt, N.; Mitin, A.; Cheprakov, A.; Kazankov, G. J.
Organomet. Chem. 2001, 622, 89. (f) Brunel, J.-M.;
Heumann, A.; Buono, G. Angew. Chem. Int. Ed. 2000, 39,
1946.
(9) For examples of Suzuki or Heck reactions using sulfur
ligands: (a) Gruber, A.; Zim, D.; Ebeling, G.; Monteiro, A.;
Dupont, J. Org. Lett. 2000, 2, 1287. (b) Zim, D.; Gruber,
A.; Ebeling, G.; Dupont, J.; Monteiro, A. Org. Lett. 2000, 2,
2881.
(10) Reddy, R.; Surekha, K.; Lee, G.-H.; Peng, S.-M.; Liu, S.-T.
Organometallics 2000, 19, 2637.
Synthesis 2001, No. 15, 2320–2326 ISSN 0039-7881 © Thieme Stuttgart · New York