274
W. Cai, D. H. Brown Ripin
LETTER
H.; Queguiner, G.; Ricci, A.; Cahiez, G.; Knochel, P.
1H NMR (CDCl3) 8.0 (d, J = 5 Hz, 1 H), 7.7 (d, J = 6 Hz, 1 H), 7.5
(s, 1 H), 7.2 (dd, J = 1.9, 8 Hz, 1 H), 0.6 (m, 2 H), 0.4 (m, 6 H). 13
NMR (CDCl3) 149.3, 144.0, 141.1, 123.6, 14.6, 9.3. mp 172.0–
175.5 °C.
C
Chem.– Eur. J. 2000, 6, 767. (c) Lepretre, A.; Turck, A.;
Ple, N.; Knochel, P.; Queguiner, G. Tetrahedron 2000, 56,
265. (d) Shimura, A.; Momotake, A.; Togo, H.; Yokoyama,
M. Synthesis 1999, 495. (e) Kondo, Y.; Yoshida, A.; Sato,
S.; Sakamoto, T. Heterocycles 1996, 42, 105. (f) Turner, R.
M.; Lindell, S. D.; Ley, S. V. J. Org. Chem. 1991, 56, 5739.
(g) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett.
1999, 40, 7449. (h) Dehmel, F.; Abarbri, M.; Knochel, P.
Synlett. 2000, 345. (i) Felding, J.; Kristensen, J.;
References
(1) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic
Chemistry; Pergamon: Oxford, 2000.
(2) (a) Ishikura, M.; Mano, T.; Oda, I.; Terashima, M.
Heterocycles 1984, 22, 2471. (b) Ishikura, M.; Ohta, T.;
Terashima, M. Chem. Pharm. Bull. 1983, 31, 4573.
(c) Morris, G. A.; Nguyen, S. T. Tetrahedron Lett. 2001, 42,
2093. (d) Labadie, S. S.; Rotstein, D. M.; Sjogren, E. B.;
Talamas, F. X. World Patent, 9957101, 1999.
(3) (a) Gilman, H.; Spatz, S. M. J. Org. Chem. 1951, 16, 1485.
(b) Mallet, M.; Branger, G.; Marsaia, F.; Quenguiner, G. J.
Organomet. Chem. 1990, 382, 319.
(4) (a) Harris, S. A. Iowa State Coll. J. Sci. 1932, 6, 425.
(b) Overhoff, J.; Proost, W. Rec. Trav. Chim. 1938, 57, 179.
(c) Proost, W.; Wibaut, J. P. Rec. Trav. Chim. 1940, 59, 971.
(d) Lai, Y.-H. Synthesis 1981, 585. (e) Nakane, M.;
Hutchinson, C. R. J. Org. Chem. 1978, 43, 3922.
(5) Magnesium halogen exchange: (a) Abarbri, M.; Thibonnet,
J.; Berillon, L.; Dehmel, F.; Rottlaender, M.; Knochel, P. J.
Org. Chem. 2000, 65, 4618. (b) Rottlander, M.; Boymond,
L.; Berillon, L.; Lepretre, A.; Varchi, G.; Avolio, S.; Laaziri,
Bjerregaard, T.; Sander, L.; Vedso, P.; Begtrup, M. J. Org.
Chem. 1999, 64, 41964.
(6) Pyridyl Grignard reagents have also been generated by
ligand exchange reactions of aryl pyridyl sulfoxides with
Grignard reagents: Shibutani, T.; Fujihara, H.; Furukawa, N.
Heteroat. Chem. 1991, 2, 521.
(7) (a) Paradies, H. H.; Gorbing, M. Angew. Chem. Int. Ed.
Engl. 1969, 8, 279. (b) Martin, G. J.; Mechin, B.; Leroux,
Y.; Paulmier, C.; Meunier, J. C. J. Organomet. Chem. 1974,
67, 327. (c) Furukawa, N.; Shibutani, T.; Fujihara, H.
Tetrahedron Lett. 1987, 28, 5845. (d) Trecourt, F.; Breton,
G.; Bonnet, V.; Mongin, F.; Marsais, F.; Queguiner, G.
Tetrahedron Lett. 1999, 40, 4339. (e) Berillon, L.; Lepretre,
A.; Turck, A.; Ple, N.; Queguiner, G.; Cahiez, G.; Knochel,
P. Synlett 1998, 1359. (f) Trecourt, F.; Breton, G.; Bonnet,
V.; Mongin, F.; Marsais, F.; Queguiner, G. Tetrahedron
2000, 56, 1349.
(8) All products have been fully characterized by spectroscopic
methods after isolation by crystallization.
Synlett 2002, No. 2, 273–274 ISSN 0936-5214 © Thieme Stuttgart · New York