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Synthesis 2009(19): 3219-3226
DOI: 10.1055/s-0029-1216944
DOI: 10.1055/s-0029-1216944
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Morita-Baylis-Hillman Reaction on Water without Organic Solvent, Assisted by a ‘Catalytic’ Amount of Amphiphilic Imidazole Derivatives
Further Information
Received
24 April 2009
Publication Date:
21 August 2009 (online)
Publication History
Publication Date:
21 August 2009 (online)
Abstract
A Morita-Baylis-Hillman (MBH) reaction using water as a solvent without any organic solvent can be performed by using an amphiphilic N-alkylimidazole. This reaction is accelerated by the addition of water and is the first example of a ‘catalytic’ MBH reaction without organic solvent in the presence of water.
Key words
Morita-Baylis-Hillman reaction - organocatalyst - water - imidazole - amphiphilic catalyst
-
1a
Rideout DC.Breslow R. J. Am. Chem. Soc. 1980, 102: 7816 -
1b
Breslow R. Acc. Chem. Res. 1991, 24: 159 -
2a
Lubineau A. Chem. Ind. 1996, 123 -
2b
Lindström UM. Chem. Rev. 2002, 102: 2751 -
2c
Lubineau A.Augé J.Queneau Y. Synthesis 1994, 741 -
2d
Li C.-J. Chem. Rev. 2005, 105: 3095 -
3a
Dong VM.Fiedler D.Carl B.Bergman RG.Raymond KN. J. Am. Chem. Soc. 2006, 128: 14464 -
3b
Vaitheeswaran S.Thirumalai D. J. Am. Chem. Soc. 2006, 128: 13490 -
4a
Larsen SD.Grieco PA. J. Am. Chem. Soc. 1985, 107: 1768 -
4b
Loncaric C.Manabe K.Kobayashi S. Chem. Commun. 2003, 574 -
4c
Ponaras AA. J. Org. Chem. 1983, 48: 3866 -
4d
Coates RM.Roger BD.Hobbs SJ.Peck DR.Curran DP. J. Am. Chem. Soc. 1987, 109: 1160 -
4e
Gajewski JJ.Jurayj J.Kimbrough DR.Gande ME.Ganem B.Carpenter BK. J. Am. Chem. Soc. 1987, 109: 1170 -
4f
Inoue Y.Araki K.Shiraishi S. Bull. Chem. Soc. Jpn. 1991, 64: 3079 -
5a
Runge MB.Mwangi MT.Miller AL.Perring M.Bowden NB. Angew. Chem. Int. Ed. 2008, 47: 935 -
5b
Cornils B.Herrmann WA. In Aqueous-Phase Organometallic Chemistry Wiley-VCH; Weinheim: 1998. -
5c
Li C.-J.Chan T.-H. In Organic Reactions in Aqueous Media John Wiley; New York: 1997. -
6a
Asano K.Matsubara S. Org. Lett. 2009, 11: 1757 -
6b
Manabe K.Sun X.-M.Kobayashi S. J. Am. Chem. Soc. 2001, 123: 10101 -
6c
Hayashi Y.Aratake S.Okano T.Takahashi J.Sumiya T.Shoji M. Angew. Chem. Int. Ed. 2006, 45: 5527 -
6d
Mase N.Nakai Y.Ohara N.Yoda H.Takabe K.Tanaka F.Barbas CF. J. Am. Chem. Soc. 2006, 128: 734 -
6e
Luo S.Mi X.Liu S.Xu H.Cheng J.-P. Chem. Commun. 2006, 3687 -
7a
Pellissier H. Tetrahedron 2007, 63: 9267 -
7b
Mukherjee S.Yang JW.Hoffmann S.List B. Chem. Rev. 2007, 107: 5471 -
7c
Pan C.Wang Z. Coord. Chem. Rev. 2008, 252: 736 -
7d
Kočovský P.Malkov AV. Pure Appl. Chem. 2008, 80: 953 -
7e
Gruttadauria M.Giacalone F.Lo Meo P.Marculescu AM.Riela S.Noto R. Eur. J. Org. Chem. 2008, 1589 -
7f
Brogan AP.Dickerson TJ.Janda KD. Angew. Chem. Int. Ed. 2006, 45: 8100 -
7g
Hayashi Y. Angew. Chem. Int. Ed. 2006, 45: 8103 -
7h
Luo S.Zhang B.He J.Janczuk A.Wang PG.Cheng J.-P. Tetrahedron Lett. 2002, 43: 7369 -
7i
Gatri R.Gaïed MME. Tetrahedron Lett. 2002, 43: 7835 -
7j
Caumul P.Hailes HC. Tetrahedron Lett. 2005, 46: 8125 -
7k
Davies HJ.Ruda AM.Tomkinson NCO. Tetrahedron Lett. 2007, 48: 1461 -
7l
Hayashi Y.Okado K.Ashimine I.Shoji M. Tetrahedron Lett. 2002, 43: 8683 -
8a
Aggarwal VK.Mereu A.Tarver GJ.McCague R. J. Org. Chem. 1998, 63: 7183 -
8b
Aggarwal VK.Dean DK.Mereu A.Williams R. J. Org. Chem. 2002, 67: 510 - 9
Asano K.Matsubara S. Synlett 2009, 35 -
10a
Basavaiah D.Rao KV.Reddy RJ. Chem. Soc. Rev. 2007, 36: 1581 -
10b
Ciganek E. Org. React. 1997, 51: 201 -
10c
Langer P. Angew. Chem. Int. Ed. 2000, 39: 3049 -
10d
Cabrera S.Alemán J.Bolze P.Bertelsen S.Jørgensen KA. Angew. Chem. Int. Ed. 2008, 47: 121 -
10e
Lin Y.-S.Liu C.-W.Tsai TYR. Tetrahedron Lett. 2005, 46: 1859 -
10f
Tang H.Zhao G.Zhou Z.Gao P.He L.Tang C. Eur. J. Org. Chem. 2008, 126 -
11a
Enders D.Balensiefer T. Acc. Chem. Res. 2004, 37: 534 -
11b
Nair V.Bindu S.Sreekumar V. Angew. Chem. Int. Ed. 2004, 43: 5130 -
11c
Suzuki Y. J. Org. Synth. Chem. Jpn. 2008, 66: 377 -
11d
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606 -
12a
Kurihara K.Kunitake T. J. Am. Chem. Soc. 1992, 114: 10927 -
12b
Matsubara S.Matsuda H.Hamatani T.Schlosser M. Tetrahedron 1988, 44: 2855 -
13a
Zhong L.Gao Q.Gao JB.Xiao J.Li C. J. Catal. 2007, 250: 360 -
13b
Li J.Zhang Y.Han D.Jia G.Gao J.Zhong L.Li C. Green Chem. 2008, 10: 608 - 14
Narayan S.Muldoon J.Finn MG.Fokin VV.Kolb HC.Sharpless KB. Angew. Chem. Int. Ed. 2005, 44: 3275 - 15
Khabnadideh S.Rezaei Z.Khalafi-Nezhad A.Bahrinajafi R.Mohamadi R.Farrokhroz AA. Bioorg. Med. Chem. Lett. 2003, 13: 2863 - 16
Vitz J.Mac DH.Legoupy S. Green Chem. 2007, 9: 431