Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2007(6): 853-856
DOI: 10.1055/s-2007-965936
DOI: 10.1055/s-2007-965936
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Fast and Convenient Heck Reaction in Water under Microwave Irradiation
Further Information
Received
19 October 2006
Publication Date:
13 February 2007 (online)
Publication History
Publication Date:
13 February 2007 (online)
Abstract
A fast and convenient base-free Heck reaction of acrylic acid and allyl alcohol with hypervalent iodonium salts was achieved under microwave irradiation in water, providing a simple method for synthesis of trans-cinnamic acids and trans-cinnamyl alcohols in good yields in short time.
Key words
Heck reaction - hypervalent iodonium salts - microwave irradiation - trans-cinnamic acids
-
1a
Heck RF. Org. React. 1982, 27: 345 -
1b
Heck RF. Acc. Chem. Res. 1979, 12: 146 -
1c
de Meijere A.Meyer FE. Angew. Chem., Int. Ed. Engl. 1994, 33: 2379 -
1d
Davis GD.Hallbery A. Chem. Rev. 1989, 89: 1433 -
2a
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997. -
2b
Varvoglis A. Tetrahedron 1997, 53: 1179 -
2c
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 96: 1123 -
2d
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 -
2e
Wirth T.Hirt UH. Synthesis 1999, 1271 -
2f
Kirschning A. Eur. J. Org. Chem. 1998, 2267 -
2g
Kitamura T.Fujiwara Y. Org. Prep. Proced. Int. 1997, 29: 409 -
2h
Moriarty RM.Prakasa O. Org. React. 1999, 54: 273 -
2i
Ochiai M. In Chemistry of Hypervalent CompoundsAkibe K. VCH; New York: 1999. Chap. 13. p.359-387 -
2j
Ochiai M. J. Organomet. Chem. 2000, 611: 494 -
2k
Okuyama T. Acc. Chem. Res. 2002, 35: 12 -
2l
Zhdankin VV.Stang PJ. Tetrahedron 1998, 54: 10927 -
2m
Grushin VV. Chem. Soc. Rev. 2000, 29: 315 -
3a
Ochiai M.Sumi K.Takaoka Y.Kurishima M.Nagao Y.Shiro M.Fujita E. Tetrahedron 1988, 44: 4095 -
3b
Ochiai M.Oshima K.Masiki Y. Tetrahedron Lett. 1991, 32: 7711 -
3c
Okuyama T.Takino T.Sueda T.Ochiai M. J. Am. Chem. Soc. 1995, 117: 3360 -
3d
Yan J.Chen ZC. Synth. Commun. 2000, 30: 1009 -
4a
Bumagin NA.Sukhomlinova LI.Banchikov AN.Tolstaya TP.Beletskaya IP. Russ. Chem. Bull. 1992, 41: 2130 -
4b
Moriarty RM.Epa WR.Awasthi AK. J. Am. Chem. Soc. 1991, 113: 6315 -
4c
Hinkle RJ.Poulter GT.Stang PJ. J. Am. Chem. Soc. 1993, 115: 11626 -
4d
Kang S.-K.Jung K.-Y.Park C.-H.Jang S.-B. Tetrahedron Lett. 1995, 36: 8047 -
4e
Kang S.-K.Lee H.-W.Jang S.-B.Kim T.-H.Pyun S.-J. J. Org. Chem. 1996, 61: 2604 -
5a
Caddick S. Tetrahedron 1995, 51: 10403 -
5b
Galema SA. Chem. Soc. Rev. 1997, 26: 223 -
5c
Lidstrom P.Tierney J.Wathry B.Westman J. Tetrahedron 2001, 57: 9225 -
5d
Kuhnert N. Angew. Chem. Int. Ed. 2002, 41: 1863 -
6a
Deshayes S.Liagre M.Loupy A. Tetrahedron 1999, 55: 10851 -
6b
Arvela RK.Leadbeater NE. J. Org. Chem. 2005, 70: 1786 -
6c
Wang J.-X.Liu Z.Hu Y.Wei B.Bai L. J. Chem. Res., Synop. 2000, 484 -
7a
Yan J.Zhu M.Zhou Z.-S. Eur. J. Org. Chem. 2006, 2060 -
7b
Yan J.Zhou Z.-S.Zhu M. Synth. Commun. 2006, 36: 1495 -
8a
Kang S.-K.Lee H.-W.Jang S.-B.Ho P.-S. J. Org. Chem. 1996, 61: 4720 -
8b
Miyaura N.Yamada K.Suginome H.Suzuki A. J. Am. Chem. Soc. 1985, 107: 972 -
9a
Jones G. Org. React. 1967, 15: 204 -
9b
Tietze LF.Beifuss U. Comprehensive Organic Synthesis Vol. 2:Trost BM.Flemming I.Heathcock C. H. Pergamon Press; Oxford: 1991. p.341 - 10
Beringer FM.Drexler M.Gindler EM.Lumpkin CC. J. Am. Chem. Soc. 1953, 75: 2705 - 11
Beringer FM.Drexler M.Gindler EM.Lumpkin CC. J. Am. Chem. Soc. 1959, 81: 4321 - 12
Margida AJ.Koser GF. J. Org. Chem. 1984, 49: 3643 - 13
Ochiai M.Sumi K.Takaoka Y.Nagao Y.Shiro M.Fujita E. Tetrahedron 1988, 44: 4095 - 14
Britteri DR. J. Org. Chem. 1981, 46: 2514 - 15
Cai MZ.Song CS.Hiang X. Synthesis 1997, 521 - 16
Beilsteins Handbuch der Organischen Chemie
Springer;
Berlin:
1983.
4th ed., EIV, Vol. 9:
p.597
- 17
Mogilaiah K.Reddy R. Synth. Commun. 2004, 34: 205 - 18
Kang S.-K.Lee H.-W.Jang S.-B.Kim T.-H.Pyum S.-J. J. Org. Chem. 1996, 61: 2604 - 19
Avery TD.Caiazza D.Culbert JA.Taylor DK.Tiekink ERT. J. Org. Chem. 2005, 70: 8344 - 20
Bellassoued M.Lensen N.Bakasse M.Mouelhi S.
J. Org. Chem. 1998, 63: 8785 - 21
Clough MS.Gupton JT.Driscoll DR.Griffin KA.Hewitt AM.Hudson MS.Ligali SA.Mulcahy SP.Roberts MN.Miller RB.Belachew TT.Kamenova ID.Kanters RPF.Norwood BK. Tetrahedron 2004, 60: 10165