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Synthesis 2008(5): 795-799
DOI: 10.1055/s-2008-1032184
DOI: 10.1055/s-2008-1032184
PAPER
© Georg Thieme Verlag Stuttgart · New York
Copper(I) Oxide Catalyzed N-Arylation of Azoles and Amines with Arylboronic Acid at Room Temperature under Base-Free Conditions
Weitere Informationen
Received
17 October 2007
Publikationsdatum:
18. Februar 2008 (online)
Publikationsverlauf
Publikationsdatum:
18. Februar 2008 (online)
Abstract
N-Arylation of azoles and amines with arylboronic acids was efficiently carried out with heterogeneous copper(I) oxide in methanol at room temperature under base-free conditions. The products N-arylazoles and N-arylamines were isolated in good to excellent yields. A variety of arylboronic acids and amines were converted to the corresponding N-arylazoles and N-arylamines, demonstrating the versatality of the reaction.
Key words
copper(I) oxide - N-arylimidazoles - N-arylamines - N-arylation - heterogeneous catalyst
-
1a
Quan ML.Lam PYS.Han Q.Pinto DJP.He MY.Li R.Ellis CD.Clark CG.Teleha CA.Sun JH.Alexander RS.Bai S.Luettgen JM.Knabb RM.Wong PC.Wexler RR. J. Med. Chem. 2005, 48: 1729 -
1b
Dyck B.Goodfellow VS.Phillips T.Grey J.Haddach M.Rowbottom M.Naeve GS.Brown B.Saunders J. Bioorg. Med. Chem. Lett. 2004, 14: 1151 -
1c
Smallheer JM.Alexander RS.Wang J.Wang S.Nakajima S.Rossi KA.Smallwood A.Barbera F.Burdick D.Luettgen JM.Knabb RM.Wexler RR.Jadhav PK. Bioorg. Med. Chem. Lett. 2004, 14: 5263 -
1d
Venkatesan AM.Gu Y.Santos OD.Abe T.Agarwal A.Yang Y.Petersen PJ.Weiss WJ.Mansour TS.Nukaga M.Hujer AM.Bonomo RA.Knox JR. J. Med. Chem. 2004, 47: 6556 -
1e
Lange JHM.van Stuivenberg HH.Coolen HKAC.Adolfs TJP.McCreary AC.Keizer HG.Wals HC.Veerman W.Borst AJM.de Looff W.Verveer PC.Kruse CG. J. Med. Chem. 2005, 48: 1823 -
1f
Barchechath SD.Tawatao RI.Corr M.Carson DA.Cottam HB. J. Med. Chem. 2005, 48: 6409 -
1g
Mano T.Stevens RW.Kazuo A.Nakao YO.Sakakibara M.Okumura TT.Miyamoto K. Bioorg. Med. Chem. 2003, 11: 3879 -
1h
Mano T.Okumura Y.Sakakibara M.Okumura T.Tamura T.Miyamoto K.Stevens RW. J. Med. Chem. 2004, 47: 720 -
1i
Roppe J.Smith ND.Huang D.Tehrani L.Wang B.Anderson J.Brodkin J.Chung J.Jiang X.King C.Munoz B.Varney MA.Prasit P.Cosford NDP. J. Med. Chem. 2004, 47: 4645 -
1j
Voets M.Antes I.Scherer C.Muller-Viera U.Biemel K.Barassin C.Marchais-Oberwinkler S.Hartmann RW. J. Med. Chem. 2005, 48: 6632 -
2a
Iizuka K.Akahane K.Momose DI.Nakazawa M.Tanouchi T.Kawamura M.Ohyama I.Kajiwara I.Ignchi Y.Okada T.Taniguchi K.Miyamoto T.Hayashi M. J. Med. Chem. 1981, 24: 1139 -
2b
Cozzi P.Carganico G.Fusar D.Grossoni M.Menichincheri M.Pinciroli V.Tonani R.Vaghi F.Salvati P. J. Med. Chem. 1993, 36: 2964 -
2c
Wolfe J.Marcoux J.-F.Buchwald SL. Acc. Chem. Res. 1998, 31: 805 -
2d
Hartwig JF. Acc. Chem. Res. 1998, 31: 853 -
3a
Gungor T.Fouquet A.Teulon J.-M.Prevost D.Cazes M.Cloarec A. J. Med. Chem. 1992, 35: 4455 -
3b
Venuti MC.Stephenson RA.Alvarez R.Bruno JJ.Strosberg AM. J. Med. Chem. 1988, 31: 2136 -
3c
Ohmori J.Shimizu-Sasamata M.Okada M.Sakamoto SJ. J. Med. Chem. 1996, 39: 3971 -
4a
Martinez GR.Walker KAM.Hirshfeld DR.Bruno JJ.Yang DS.Maloney PJJ. J. Med. Chem. 1992, 35: 620 -
4b
Lo YS.Nolan JC.Maren TH.Welstead JR.Gripshover DF.Shamblee DA. J. Med. Chem. 1992, 35: 4790 -
4c
Pavik WJJW.Connors RE.Burns DS.Kurzweil EM. J. Med. Chem. 1993, 115: 7645 -
5a
Lam PYS.Deudon S.Averill KM.Li R.He MY.Deshong P.Clark CG. J. Am. Chem. Soc. 2000, 122: 7600 -
5b
Elliott GI.Konopelski JP. Org. Lett. 2000, 2: 3055 -
5c
Lopez-Alvarado P.Avendano C.Menendez JC. J. Org. Chem. 1996, 61: 5865 -
5d
Lopez-Alvarado P.Avendano C.Menendez JC. Tetrahedron Lett. 1992, 33: 659 -
6a
Lam PYS.Clark CG.Saubern S.Adams J.Winters MP.Chan DMT.Combs A. Tetrahedron Lett. 1998, 39: 2941 -
6b
Combs AP.Saubern S.Rafalski M.Lam PYS. Tetrahedron Lett. 1999, 40: 1623 -
6c
Lam PYS.Clark CG.Saubern S.Adams J.Averill KM.Chan DMT.Combs A. Synlett 2000, 674 -
7a
Collman JP.Zhong M.Zeng L.Costanzo S. J. Org. Chem. 2001, 66: 1528 -
7b
Collman JP.Zhong M. Org. Lett. 2000, 2: 1233 - 8
Lan J.-B.Chen L.Yu X.-Q.You J.-S.Xie R.-G. Chem. Commun. 2004, 188 - 9
van Berkel SS.van den Hoogenband A.Terpstra JW.Tromp M.van Leeuwen PWNM.van Strijdonck GPF. Tetrahedron Lett. 2004, 45: 7659 -
10a
Choudary BM.Sridhar Ch.Kantam ML.Venkanna GT.Sreedhar B. J. Am. Chem. Soc. 2005, 127: 9948 -
10b
Kantam ML.Venkanna GT.Sridhar Ch.Shiva Kumar KB. Tetrahedron Lett. 2006, 47: 3897 -
10c
Kantam ML.Venkanna GT.Sridhar C.Sreedhar B.Choudary BM. J. Org. Chem. 2006, 71: 9522