Biomedical Engineering Reference
In-Depth Information
Trans
.
2009
, 5820-5831; (e) D. Balcells, E. Clot, O. Eisenstein,
Chem. Rev.
2010
,
110
, 749-823
(see also Ref. [4a]).
8. For reviews on traditional transition metal-catalyzed cross-coupling reactions, see (a) J. Hassan,
M. S´vignon, C. Gozzi, E. Schulz, M. Lemaire,
Chem. Rev. 2002
,
102
, 1359-1470; (b) F.
Diederich, P. J. Stang (Eds),
Metal-Catalyzed Cross-Coupling Reactions
, Wiley-VCH, New York,
2004
.
9. For selected reviews on direct arylation, see (a) L.-C. Campeau, D. R. Stuart, K. Fagnou,
Aldrichchim.
Acta 2007
,
40
, 35-41; (b) T. Satoh, M. Miura,
Chem. Lett. 2007
,
36
, 200-205; (c) D. Alberico, M. E.
Scott, M. Lautens,
Chem. Rev. 2007
,
107
, 174-238; (d) L. Ackermann, R. Vicente, A. R. Kapdi,
Angew. Chem., Int. Ed. 2009
,
48
, 9792-9826; (e) F. Bellina, R. Rossi,
Tetrahedron 2009
,
65
,
10269-10310 (see also Ref. [1f]).
10. For selected reviews on ligand-directed C-Hbond functionalization, see (a) J.-Q. Yu, R. Giri, X. Chen,
Org. Biomol. Chem. 2006
,
4
, 4041-4047; (b) O. Daugulis, H.-Q. Do, D. Shabashov,
Acc. Chem. Res.
2009
,
42
, 1074-1086 (see also Ref. [1l]).
11. For selected references, see (a) S. Pivsa-Art, T. Satoh, Y. Kawamura, M. Miura, M. Nomura,
Bull.
Chem. Soc. Jpn. 1998
,
71
, 467-473; (b) C.-H. Park, V. Ryabova, I. V. Seregin, A. W. Sromek, V.
Gevorgyan,
Org. Lett. 2004
,
6
, 1159-1162; (c) B. S. Lane, M. A. Brown, D. Sames,
J. Am. Chem. Soc.
2005
,
127
, 8050-8057.
12. For selected references, see (a) D. Garcia-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren,
J. Am. Chem. Soc.
2006
,
128
, 1066-1067; (b) M. Lafrance, C. N. Rowley, T. K. Woo, K. Fagnou,
J. Am. Chem. Soc.
2006
,
128
, 8754-8756; (c) D. Lapointe, K. Fagnou,
Chem. Lett.
2010
,
39
,
1118-1126 and references therein.
13. (a) S. I. Gorelsky, D. Lapointe, K. Fagnou,
J. Am. Chem. Soc.
2008
,
130
, 10848-10849; (b) B.
2010
,
75
, 1047-1060.
14. For selected examples, see (a) P. P. Deshpande, O. R. Martin,
Tetrahedron Lett
.
1990
,
31
, 6313-6316;
(b) G. Bringmann, M. Ochse, R. Gotz,
J. Org. Chem.
Li´gault, I. Petrov, S. I. Gorelsky, K. Fagnou,
J. Org. Chem.
2000
,
65
, 2069-2077; (c) G. D. Cuny,
Tetrahedron Lett
.
2003
,
44
, 8149-8152; (d) M. Lafrance, N. Blaquiere, K. Fagnou,
Chem. Commun.
2004
, 2874-2875; (e) G. D. Cuny,
Tetrahedron Lett
.
2004
,
45
, 5167-5170; (f) A. L. Bowie, Jr., C. C.
Hughes, D. Trauner,
Org. Lett.
2005
,
7
, 5207-5209; (g) M. Lafrance, N. Blaquiere, K. Fagnou,
Eur. J.
Org. Chem. 2007
, 811-825.
15. (a) T. Oki, M. Konishi, K. Tomatsu, K. Tomita, K.-I. Saitoh, M. Tsunakawa, M. Nishio, T. Miyaki, H.
Kawaguchi,
J. Antibiot. 1988
,
41
, 1701-1704; (b) T. Takeuchi, T. Hara, H. Naganawa, M. Okada, M.
Hamada, H. Umezawa, S. Gomi, M. Sezaki, S. Kondo,
J. Antibiot. 1988
,
41
, 807-811; (c) J. C. Fung-
Tomc, D. P. Bonner,
Exp. Opin. Invest. Drugs 1997
,
6
, 129-145; (d) A. Baranczak, G. A. Sulikowski,
Angew. Chem., Int. Ed. 2009
,
48
, 6005-6007.
16. M. Kitamura, K. Ohmori, T. Kawase, K. Suzuki,
Angew. Chem., Int. Ed. 1999
,
38
, 1229-1232.
17. Suzuki and coworkers had previously found that sodium pivalate was the optimal base for
carbon-carbon bond formation
via
direct arylation in their synthesis of gilvocarcin V. Isolation of
reaction by-products determined that the use of sodium acetate led to acyl exchange due to the
nucleophilic attack of the ester moiety by the acetate anion. See T. Hosoya, E. Takashiro,
T. Matsumoto, K. Suzuki,
J. Am. Chem. Soc. 1994
,
116
, 1004-1015.
18. For seminal examples of intramolecular direct arylation, see (a) D. E. Ames, D. Bull,
Tetrahedron
1982
,
38
, 383-387; (b) D. E. Ames, A. Opalko,
Synthesis 1983
, 234-235; (c) D. E. Ames, A. Opalko,
Tetrahedron 1984
,
40
, 1919-1925.
19. For other early examples of the use of direct arylation in total synthesis, see (a) G. Bringmann, J. R.
Jansen, H.-P. Rink,
Angew. Chem., Int. Ed. Engl. 1986
,
25
, 913-915; (b) G. Bringmann, J. R. Jansen,
H. Reuscher, M. Rubenacker,
Tetrahedron Lett
.
1990
,
31
, 643-646 (see also Ref. [16]).
20. M. Leblanc, K. Fagnou,
Org. Lett.
2005
,
7
, 2849-2852.
21. For prior work on Pd(0)-catalyzed seven-membered ring formation
via
direct arylation using an aryl
bromide, see L.-C. Campeau, M. Parisien, M. Leblanc, K. Fagnou,
J. Am. Chem. Soc.
2004
,
126
,
9186-9187.
22. A. V. Vorogushin, A. V. Predeus, W. D. Wulff, H.-J. Hansen,
J. Org. Chem.
,
68
, 5826-5831.
23. For selected reviews on the Mizoroki-Heck reaction, see (a) I. P. Beletskaya, A. V. Cheprakov,
Chem.
Rev.
2003
2000
,
100
, 3009-3066; (b) M. Oestreich (Ed.),
The Mizoroki-Heck Reaction
, Wiley, Hoboken,
2009
.
Search WWH ::
Custom Search