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Synthesis 2003(4): 0551-0554
DOI: 10.1055/s-2003-37663
DOI: 10.1055/s-2003-37663
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Formylphenylpyridinecarboxylic Acids Using Suzuki-Miyaura Coupling Reactions
Further Information
Received
7 November 2002
Publication Date:
07 March 2003 (online)
Publication History
Publication Date:
07 March 2003 (online)
Abstract
Formylphenylboronic acids were coupled with bromopyridylcarboxylic acids in the presence of a palladium catalyst. The yields of the different biaryls are strongly dependant on the substitution pattern of the two coupling partners. The electronic and steric effects of these are discussed.
Key words
cross-coupling - palladium catalyst - biaryls - heterocycles - pyridine carboxylic acids
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1a
Criscione L.de Gasparo M.Buhlmayer P.Whitebread S.Ramjoue HP.Wood J. Br. J. Pharmacol. 1993, 110: 761 -
1b
Markham A.Goa KL. Drugs 1997, 54: 299 -
2a
Capdeville R.Buchdunger E.Zimmermann J.Matter A. Nat. Rev. Drug Discovery 2002, 1: 493 -
2b
Boren J.Cascante M.Marin S.Comin-Anduix B.Centelles JJ.Lim S.Bassilian S.Ahmed S.Lee WN.Boros LG. J. Biol. Chem. 2001, 276: 37747 - 3
Hassan J.Sévignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 -
4a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
4b
Suzuki A. In Metal-catalyzed Cross-coupling ReactionsDiederich F.Stang PJ. Wiley-VCH; Weinheim: 1998. p.49 -
4c
Miyaura N. Adv. Organomet. Chem. 1998, 6: 187 -
5a
Stille JK. Angew. Chem. Int. Ed. 1998, 25: 508 -
5b
Farina V.Krishnamurthy V.Scott WJ. Org. React. 1997, 50: 1 -
5c
Mitchell TN. In Metal-catalyzed Cross-coupling ReactionsDiederich F.Stang PJ. Wiley-VCH; Weinheim: 1998. p.167 -
6a
Reyes-Rivera HM.Hutchins RoO.Dalton DR. J. Heterocycl. Chem. 1995, 32: 665 -
6b
Fevig JM.Pinto DJ.Han Q.Quan ML.Pruitt JR.Jacobson IC.Galemmo RA.Wang S.Orwat MJ. Bioorg. Med. Chem. Lett. 2001, 11: 641 -
6c
Bradlow HL.Vanderwerf CA. J. Org. Chem. 1949, 14: 509 - 7
Bumagin NA.Bykov VV. Tetrahedron 1997, 53: 14437 - 8 Due to the different solubility
properties of the formyl-phenylpyridinecarboxylic acids the products
could be isolated more or less well after the Suzuki-Miyaura coupling.
Therefore the yields do not reflect exactly the conversion of the
reactions.
- 9
Heck RF. In Palladium Reagents in Organic Synthesis Academic Press; New York: 1985. - 10
Rocek J.Peng TY. J. Am. Chem. Soc. 1977, 99: 7622