Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2003(12): 1892-1894
DOI: 10.1055/s-2003-41460
DOI: 10.1055/s-2003-41460
LETTER
© Georg Thieme Verlag Stuttgart · New York
New Cobalt-Catalyzed Cross-Coupling Reactions of Heterocyclic Chlorides with Aryl and Heteroaryl Magnesium Halides
Further Information
Received
7 July 2003
Publication Date:
19 September 2003 (online)
Publication History
Publication Date:
19 September 2003 (online)
Abstract
New cobalt-catalyzed cross-coupling between arylmagnesium halides and 2-chloropyridines and related heterocycles occur at low temperature leading to 2-arylated heterocycles in good yields.
Key words
cobalt-catalysis - cross-coupling - organomagnesium reagents - arylation - heterocycles
-
1a
Diederich F.Stang PJ. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1998. -
1b
Miyaura N. Cross-Coupling Reactions. A Practical Guide Springer; Berlin: 2002. - 2
Li JJ.Gribble GW. Palladium in Heterocyclic Synthesis Vol. 20: Tetrahedron Organic Chemistry Series, Pergamon; Amsterdam: 2000. - For excellent reviews of palladium cross-coupling reactions, see:
-
3a
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 -
3b
Whitcombe NJ.Hii KK.Gibson SE. Tetrahedron 2001, 57: 7449 -
3c
Beletskaya IP.Cheprakov AV. Chem. Rev. 2000, 100: 3009 -
3d
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
4a
Li GY.Marshall WJ. Organometallics 2002, 21: 590 -
4b
Wu J.Yang Z. J. Org. Chem. 2001, 66: 7875 -
4c
Srogl J.Liu W.Marshall D.Liebeskind LS. J. Am. Chem. Soc. 1999, 121: 9949 -
4d
Erdelmeier I.Gais HJ. J. Am. Chem. Soc. 1989, 111: 1125 -
4e
Tasler S.Lipshutz BH. J. Org. Chem. 2003, 68: 1190 -
4f
Lipshutz BH.Blomgren PA. J. Am. Chem. Soc. 1999, 121: 5819 -
4g
Kiso Y.Tamao K.Kumada M. J. Organomet. Chem. 1973, 50: C 12 -
5a
Fürstner A.Leitner A.Méndez M.Krause H. J. Am. Chem. Soc. 2002, 124: 13856 -
5b
Quintin J.Frank X.Hocquemiller R.Figadère B. Tetrahedron Lett. 2002, 43: 3547 -
5c
Tamura M.Kochi JK. J. Am. Chem. Soc. 1971, 93: 1487 -
5d
Tamura M.Kochi JK. Synthesis 1971, 303 -
5e
Neumann SM.Kochi JK. J. Org. Chem. 1975, 40: 599 -
5f
Smith RS.Kochi JK. J. Org. Chem. 1976, 41: 502 -
5g
Kochi JK. Acc. Chem. Res. 1974, 7: 351 -
6a
Cahiez G.Avedissian H. Synthesis 1998, 1199 -
6b
Cahiez G.Marquais S. Pure Appl. Chem. 1996, 68: 53 -
6c
Dohle W.Kopp F.Cahiez G.Knochel P. Synlett 2001, 1901 -
6d
Molander GA.Rahn BJ.Shubert DC.Bonde SE. Tetrahedron Lett. 1983, 24: 5449 -
7a
Hodgson DM.Witherington J.Moloney BA.Richards LC.Brayer J.-L. Synlett 1995, 32 -
7b
Le Gall E.Gosmini C.Nedelec J.-Y.Périchon J. Tetrahedron Lett. 2001, 42: 267 -
7c
Gomes P.Fillon H.Gosmini C.Labbé E.Périchon J. Tetrahedron 2002, 58: 8417 -
8a
Cahiez G.Avedissian H. Tetrahedron Lett. 1998, 39: 6159 -
8b
Avedissian H.Bérillon L.Cahiez G.Knochel P. Tetrahedron Lett. 1998, 39: 6163 - For palladium catalyzed cross-coupling reactions using 2-halopyridines and related derivatives, see:
-
9a
Trécourt F.Gervais B.Mallet M.Quéguiner G. J. Org. Chem. 1996, 61: 1673 -
9b
Turck A.Plé N.Leprêtre-Gaquère A.Quéguiner G. Heterocycles 1998, 49: 205 -
9c
Bonnet V.Mongin F.Trécourt F.Quéguiner G.Knochel P. Tetrahedron Lett. 2001, 42: 5717 -
9d
Gros P.Fort Y. Synthesis 1999, 754 -
9e
Savage SA.Smith AP.Fraser CL. J. Org. Chem. 1998, 63: 10048 -
9f
Fang Y.-Q.Hanan GS. Synlett 2003, 852 - For the preparation of functionalized arylmagnesium compounds, see:
-
10a
Boymond L.Rottländer M.Cahiez G.Knochel P. Angew. Chem. Int. Ed. 1998, 37: 1701 -
10b
Varchi G.Kofink C.Lindsay DM.Ricci A.Knochel P. Chem. Commun. 2003, 396 -
10c
Sapountzis I.Knochel P. Angew. Chem. Int. Ed. 2002, 41: 1610
References
Commercially cobalt powder was used (Aldrich, 99.9+% purity).
12Commercially iron powder was used (Merck, 99.5% purity).