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Synthesis 2009(18): 3094-3098
DOI: 10.1055/s-0029-1216942
DOI: 10.1055/s-0029-1216942
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Suzuki Coupling of Heteroaromatic Chlorides Using Highly Electron-Donating ClickPhos Ligands
Further Information
Received
18 March 2009
Publication Date:
14 August 2009 (online)
Publication History
Publication Date:
14 August 2009 (online)

Abstract
Using highly electron-rich monophosphine ligands, Suzuki cross-coupling of heteroaromatic chlorides with various boronic acids was carried out in high yields. High yields were also often observed when steric heteroaromatic chlorides were employed in Suzuki cross-coupling reactions.
Key words
Suzuki coupling - ClickPhos - heteroaromatic chlorides - palladium
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Miyaura N.Suzuki A. Chem. Rev. 1996, 95: 2457 -
1b
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 1290 -
1c
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
1d
Diederich F.Stang PJ. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1998. -
1e
de Meijere A.Diederich F. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 2004. -
2a
Dehmel F.Molander GA. J. Am. Chem. Soc. 2004, 33: 10313 -
2b
Durham TB.Blanchard N.Savall B.Noel A.Roush WR. J. Am. Chem. Soc. 2006, 126: 9307 -
3a
Christmann U.Vilar R. Angew. Chem. Int. Ed. 2005, 44: 366 -
3b
Miura M. Angew. Chem. Int. Ed. 2004, 43: 2201 -
4a
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 -
4b
Barder TE.Walker SD.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4685 -
5a
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 124: 4020 -
5b
Netherton MR.Dai C.Neuschutz K.Fu GC. J. Am. Chem. Soc. 2001, 123: 10099 -
5c
Kirchhoff JH.Netherton MR.Hills ID.Fu GC. J. Am. Chem. Soc. 2002, 124: 13662 -
5d
Kudo N.Perseghini M.Fu GC. Angew. Chem. Int. Ed. 2006, 45: 1282 -
6a
Wolfe JP.Tomori H.Sadighi JP.Yin J.Buchwald SL. J. Org. Chem. 2000, 65: 1158 -
6b
Yin J.Rainka MP.Zhang X.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 1162 -
6c
Nguyen HN.Huang X.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 11818 -
6d
Walker SD.Barder TE.Martinelli JR.Buchwald SL. Angew. Chem. Int. Ed. 2004, 43: 1871 -
6e
Barder TE.Walker SD.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4685 -
6f
Billingsley KL.Anderson KW.Buchwald SL. Angew. Chem. Int. Ed. 2006, 45: 3484 -
6g
Billingsley K.Buchwald SL. J. Am. Chem. Soc. 2007, 129: 3358 -
7a
Stambuli JP.Kuwano R.Hartwig JF. Angew. Chem. Int. Ed. 2002, 41: 4746 -
7b
Kataoka N.Shelby Q.Stambuli JP.Hartwig JF. J. Org. Chem. 2002, 67: 5553 -
8a
Zapf A.Jackstell R.Rataboul F.Reirmeier T.Monsees A.Fuhrmann C.Shaikh N.Dingerdissen U.Beller M. Chem. Commun. 2004, 38 -
8b
Harkal S.Rataboul F.Zapf A.Fuhrmann C.Reirmeier T.Monsees A.Beller M. Adv. Synth. Catal. 2004, 346: 1742 -
8c For a review, see:
Zapf A.Beller M. Chem. Commun. 2005, 431 -
9a
Dai Q.Gao W.Liu D.Zhang X. Org. Lett. 2005, 7: 4907 -
9b
Dai D.Gao W.Liu D.Kapes LM.Zhang X. J. Org. Chem. 2006, 71: 3928 -
10a
Kudo N.Perseghini M.Fu GC. Angew. Chem. Int. Ed. 2006, 45: 1282 -
10b
Billingsley KL.Anderson KW.Buchwald SL. Angew. Chem. Int. Ed. 2006, 45: 3484 -
10c
Guram AS.King AO.Allen JG.Wang X.Schenkel LB.Chan J.Bunel EE.Faul MM.Larsen RD.Martinelli MJ.Reider PJ. Org. Lett. 2006, 8: 1787 -
10d
Billingsley K.Buchwald SL. J. Am. Chem. Soc. 2007, 129: 3358 -
10e
Yamamoto Y.Takizawa M.Yu XQ.Miyaura N. Angew. Chem. Int. Ed. 2008, 47: 928