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Synlett 2002(9): 1523-1525
DOI: 10.1055/s-2002-33508
DOI: 10.1055/s-2002-33508
LETTER
© Georg Thieme Verlag Stuttgart · New York
N-Ethylpiperidine Hypophosphite Mediated Intermolecular Radical Carbon-Carbon Bond Forming Reaction in Water
Further Information
Received
3 July 2002
Publication Date:
17 September 2002 (online)
Publication History
Publication Date:
17 September 2002 (online)
Abstract
N-Ethylpiperidine hypophosphite mediated radical addition reactions to electron deficient alkenes in aqueous media have been developed. The reactions afford high isolated yields of addition products without using a large excess of alkenes.
Key words
radical reactions - addition reactions - alkenes - alkyl halides - water
-
1a
Giese B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds Pergamon Press; Oxford: 1986. -
1b
Curran DP. Synthesis 1988, 417 -
1c
Curran DP. Synthesis 1988, 479 -
1d
Curran DP. In Comprehensive Organic Synthesis Vol. 4:Trost BM.Fleming I. Pergamon; Oxford: 1991. p.715 -
1e
Motherwell W.Crich D. Free Radical Chain Reactions in Organic Synthesis Academic Press; London: 1992. - For recent reviews:
-
2a
Baguley PA.Walton JC. Angew. Chem. Int. Ed. 1998, 37: 3072 -
2b
Studer A.Amrein S. Synthesis 2002, 835 -
3a
Barton DHR.Jang DO.Jaszberenyi JC. Tetrahedron Lett. 1992, 33: 5709 -
3b
Barton DHR.Jang DO.Jaszberenyi JC. J. Org. Chem. 1993, 58: 6838 -
3c
McCague R.Pritchard RG.Stoodley RJ.Williamson DS. Chem. Commun. 1998, 2691 -
3d
Tokuyama H.Yamashita T.Reding MT.Kaburagi Y.Fukuyama T. J. Am. Chem. Soc. 1999, 121: 3791 -
3e
Graham SR.Murphy JA.Coates D. Tetrahedron Lett. 1999, 40: 2415 -
3f
Graham SR.Murphy JA.Kennedy AR. J. Chem. Soc., Perkin Trans. 1 1999, 3071 -
3g
Jang DO.Song SH. Tetrahedron Lett. 2000, 41: 247 -
3h
Concepcion GM.Murphy JA.Christopher RS. Tetrahedron Lett. 2000, 41: 1833 -
3i
Takamatsu S.Katayama S.Hirose N.Naito M.Izawa K. Tetrahedron Lett. 2001, 42: 7605 -
3j
Jang DO.Cho DY.Chung C.-M. Synlett 2001, 1923 -
4a
Jang DO. Tetrahedron Lett. 1996, 37: 5367 -
4b
Kita Y.Nambu H.Ramesh NG.Anikumar G.Matsugi M. Org. Lett. 2001, 3: 1157 -
4c
Jang DO.Cho DY. Synlett 2002, 631 -
5a
Graham AE.Thomas AV.Yang R. J. Org. Chem. 2000, 65: 2583 -
5b
Yorimitsu H.Shinokubo H.Oshima K. Chem. Lett. 2000, 105 -
5c
Yorimitsu H.Shinokubo H.Oshima K. Bull. Chem. Soc. Jpn. 2001, 74: 225 -
6a
Minisci F. Synthesis 1973, 1 -
6b
Breslow R.Light J. Tetrahedron Lett. 1990, 31: 2957 -
6c
Yamazaki O.Togo H.Nogami G.Yokoyama M. Bull. Chem. Soc. Jpn. 1997, 70: 2519 -
6d
Maitra U.Sarma KD. Tetrahedron Lett. 1994, 35: 7861 -
6e
Nambu H.Hata K.Matsugi M.Kita Y. Chem. Commun. 2002, 1082 -
6f For a recent review:
Yorimitsu H.Shinokubo H.Oshima K. Synlett 2002, 674 -
7a
Li C.-J.Chan T.-H. Organic Reactions in Aqueous Media John Wiley and Sons; New York: 1997. -
7b
Grieco PA. Organic Synthesis in Water Blackie Academic and Professional; London: 1998. -
7c
Lubineau A.Auge J. In Modern Solvents in Organic SynthesisKnochel P. Springer-Verlag; Berlin: 1999. - 9
Brown HC.Midland MM. Angew. Chem., Int. Ed. Engl. 1972, 11: 692
References
For intramolecular C-C bond formation in water, see ref. [4b]