RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2004(6): 1095-1097
DOI: 10.1055/s-2004-820059
DOI: 10.1055/s-2004-820059
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Simple Copper Salt Catalyzed N-Arylation of Amines, Amides, Imides, and Sulfonamides with Arylboronic Acids
Weitere Informationen
Received
16 February 2004
Publikationsdatum:
25. März 2004 (online)
Publikationsverlauf
Publikationsdatum:
25. März 2004 (online)
Abstract
A simple copper salt catalyzed N-arylation reaction with arylboronic acids is reported. In the presence of a catalytic amount of a simple copper salt, the coupling of arylboronic acids with imides was performed in MeOH to give N-arylimides in excellent yields; a variety of amines, amides and sulfonamides could also be successfully coupled with arylboronic acids to give corresponding N-arylated products in moderate yields.
Key words
N-arylation - copper salt - boronic acid - coupling - Ullmann reaction
-
1a
Ullmann F. Ber. Dtsch. Chem. Ges. 1903, 36: 2389 -
1b
Ullmann F. Ber. Dtsch. Chem. Ges. 1904, 37: 853 -
1c
Goldberg I. Ber. Dtsch. Chem. Ges. 1906, 39: 1691 -
1d
Hassan J.Sevingnon M.Gozzi C.Shulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 -
2a
Lopez-Alvarado P.Avendano C.Mendendez JC. Tetrahedron Lett. 1992, 33: 659 -
2b
Lopez-Alvarado P.Avendano C.Mendendez JC. J. Org. Chem. 1995, 60: 5678 -
3a
Arnauld T.Barton DHR.Doris E. Tetrahedron 1997, 53: 4137 -
3b
Finet J.-P.Federov AY.Combes S.Boyer G. Curr. Org. Chem. 2002, 6: 597 - 4
Lam PYS.Vincent D.Bonne D.Clark CG. Tedrahedron Lett. 2002, 43: 3091 -
5a
Lam PYS.Deudon S.Hauptman E.Clark CG. Tetrahedron Lett. 2001, 42: 2427 -
5b
Lam PYS.Deudon S.Averill KM.Li R.He MY.DeShong P.Clark CG. J. Am. Chem. Soc. 2000, 122: 7600 -
5c
Lam PYS.Clark CG.Saubern S.Adams J.Averill KM.Chan DMT.Combs A. Synlett 2000, 674 - 6
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 -
7a
Chan DMT.Monaco KL.Wang R.-P.Winters MP. Tetrahedron Lett. 1998, 39: 2933 -
7b
Evans DA.Katz JL.West TR. Tetrahedron Lett. 1998, 39: 2937 -
7c
Lam PYS.Clark CG.Saubern S.Adams J.Winters MP.Chan DMT.Combs A. Tetrahedron Lett. 1998, 39: 2941 -
7d
Fedorov AY.Finet J.-P. Tetrahedron Lett. 1998, 39: 7979 -
8a
Collmann JP.Zhong M. Org. Lett. 2000, 2: 1233 -
8b
Collmann JP.Zhong M.Zhang C.Costanzo S. J. Org. Chem. 2001, 66: 7892 -
8c
Collmann JP.Zhong M.Zeng L.Costanzo S. J. Org. Chem. 2001, 66: 1528 -
9a
Antilla JC.Buchwald SL. Org. Lett. 2001, 3: 2077 -
9b
Sasaki M.Dalili S.Yudin AK. J. Org. Chem. 2003, 68: 2045 -
9c
Lam PYS.Vincent D.Clark CG.Deudon S.Jadhav PK. Tedrahedron Lett. 2001, 42: 3415 - 10
Lan J.-B.Chen L.Yu X.-Q.You J.-S.Xie R.-G. Chem. Commun. 2004, 188 -
11a
Chan DMT.Monaco KL.Li R.Bonne D.Clark CG.Lam PYS. Tetrahedron Lett. 2003, 44: 3863 -
11b
Lam PYS.Bonne D.Vincent G.Clark CG.Combs A. Tetrahedron Lett. 2003, 44: 1691 -
11c
Yu S.Saenz J.Srirangam JK. J. Org. Chem. 2002, 67: 1699 -
11d
Mederski WWKR.Lefort M.Germann M.Kux D. Tetrahedron 1999, 55: 12757 -
11e
Combs A.Suabern S.Rafalski M.Lam PYS. Tetrahedron Lett. 1999, 40: 1623 - 12
Quach TD.Batey RA. Org. Lett. 2003, 5: 4397