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Volumn 44, Issue 37, 2003, Pages 7027-7029

Radical-mediated hydroxytrifluoromethylation of α,β-unsaturated esters

Author keywords

Hydroxytrifluoromethylation; Radical reaction; , unsaturated esters

Indexed keywords

BORANE DERIVATIVE; ESTER DERIVATIVE; IODINE DERIVATIVE; POTASSIUM FLUORIDE; RADICAL; TRIETHYLBORANE; TRIFLUOROMETHYL IODIDE; UNCLASSIFIED DRUG; WATER;

EID: 0042158203     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01783-0     Document Type: Article
Times cited : (45)

References (31)
  • 1
    • 0027432004 scopus 로고    scopus 로고
    • For a review and books, see: (a) Resnati, G. Tetrahedron 1993, 49, 9385-9445; (b) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1990; (c) Biomedical Aspects of Fluorine Chemistry; Filler, R.; Kobayashi, Y., Eds.; Kodansha Ltd: Tokyo, 1982; (d) Kitazume, T.; Yamazaki, T. Experimental Methods in Organic Fluorine Chemistry; Kodansha Ltd: Tokyo, 1998.
    • (1993) Tetrahedron , vol.49 , pp. 9385-9445
    • Resnati, G.1
  • 2
    • 0027432004 scopus 로고    scopus 로고
    • John Wiley & Sons: New York
    • For a review and books, see: (a) Resnati, G. Tetrahedron 1993, 49, 9385-9445; (b) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1990; (c) Biomedical Aspects of Fluorine Chemistry; Filler, R.; Kobayashi, Y., Eds.; Kodansha Ltd: Tokyo, 1982; (d) Kitazume, T.; Yamazaki, T. Experimental Methods in Organic Fluorine Chemistry; Kodansha Ltd: Tokyo, 1998.
    • (1990) Fluorine in Bioorganic Chemistry
    • Welch, J.T.1    Eswarakrishnan, S.2
  • 3
    • 0027432004 scopus 로고    scopus 로고
    • Eds.; Kodansha Ltd: Tokyo
    • For a review and books, see: (a) Resnati, G. Tetrahedron 1993, 49, 9385-9445; (b) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1990; (c) Biomedical Aspects of Fluorine Chemistry; Filler, R.; Kobayashi, Y., Eds.; Kodansha Ltd: Tokyo, 1982; (d) Kitazume, T.; Yamazaki, T. Experimental Methods in Organic Fluorine Chemistry; Kodansha Ltd: Tokyo, 1998.
    • (1982) Biomedical Aspects of Fluorine Chemistry
    • Filler, R.1    Kobayashi, Y.2
  • 4
    • 0027432004 scopus 로고    scopus 로고
    • Kodansha Ltd: Tokyo
    • For a review and books, see: (a) Resnati, G. Tetrahedron 1993, 49, 9385-9445; (b) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1990; (c) Biomedical Aspects of Fluorine Chemistry; Filler, R.; Kobayashi, Y., Eds.; Kodansha Ltd: Tokyo, 1982; (d) Kitazume, T.; Yamazaki, T. Experimental Methods in Organic Fluorine Chemistry; Kodansha Ltd: Tokyo, 1998.
    • (1998) Experimental Methods in Organic Fluorine Chemistry
    • Kitazume, T.1    Yamazaki, T.2
  • 5
    • 0000836901 scopus 로고    scopus 로고
    • For a review, see: (a) Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557-1584. For triethylborane-induced reactions, see: (b) Takeyama, Y.; Ichinose, Y.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3159-3162; (c) Miura, K.; Taniguchi, M.; Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6391-6394; (d) Miura, K.; Takeyama, Y.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1542-1553. For photochemical oxyperfluoroalkylation reaction of simple alkenes using molecular oxygen, see: (e) Yoshida, M.; Ohkoshi, M.; Aoki, N.; Ohnuma, Y.; Iyoda, M. Tetrahedron Lett. 1999, 40, 5731-5734.
    • (1996) Chem. Rev. , vol.96 , pp. 1557-1584
    • Dolbier W.R., Jr.1
  • 6
    • 0001596458 scopus 로고
    • For a review, see: (a) Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557-1584. For triethylborane-induced reactions, see: (b) Takeyama, Y.; Ichinose, Y.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3159-3162; (c) Miura, K.; Taniguchi, M.; Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6391-6394; (d) Miura, K.; Takeyama, Y.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1542-1553. For photochemical oxyperfluoroalkylation reaction of simple alkenes using molecular oxygen, see: (e) Yoshida, M.; Ohkoshi, M.; Aoki, N.; Ohnuma, Y.; Iyoda, M. Tetrahedron Lett. 1999, 40, 5731-5734.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3159-3162
    • Takeyama, Y.1    Ichinose, Y.2    Oshima, K.3    Utimoto, K.4
  • 7
    • 0025119619 scopus 로고
    • For a review, see: (a) Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557-1584. For triethylborane-induced reactions, see: (b) Takeyama, Y.; Ichinose, Y.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3159-3162; (c) Miura, K.; Taniguchi, M.; Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6391-6394; (d) Miura, K.; Takeyama, Y.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1542-1553. For photochemical oxyperfluoroalkylation reaction of simple alkenes using molecular oxygen, see: (e) Yoshida, M.; Ohkoshi, M.; Aoki, N.; Ohnuma, Y.; Iyoda, M. Tetrahedron Lett. 1999, 40, 5731-5734.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6391-6394
    • Miura, K.1    Taniguchi, M.2    Nozaki, K.3    Oshima, K.4    Utimoto, K.5
  • 8
    • 0001532325 scopus 로고
    • For photochemical oxyperfluoroalkylation reaction of simple alkenes using molecular oxygen, see:
    • For a review, see: (a) Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557-1584. For triethylborane-induced reactions, see: (b) Takeyama, Y.; Ichinose, Y.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3159-3162; (c) Miura, K.; Taniguchi, M.; Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6391-6394; (d) Miura, K.; Takeyama, Y.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1542-1553. For photochemical oxyperfluoroalkylation reaction of simple alkenes using molecular oxygen, see: (e) Yoshida, M.; Ohkoshi, M.; Aoki, N.; Ohnuma, Y.; Iyoda, M. Tetrahedron Lett. 1999, 40, 5731-5734.
    • (1991) Bull. Chem. Soc. Jpn. , vol.64 , pp. 1542-1553
    • Miura, K.1    Takeyama, Y.2    Oshima, K.3    Utimoto, K.4
  • 9
    • 0033618294 scopus 로고    scopus 로고
    • For a review, see: (a) Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557-1584. For triethylborane-induced reactions, see: (b) Takeyama, Y.; Ichinose, Y.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3159-3162; (c) Miura, K.; Taniguchi, M.; Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6391-6394; (d) Miura, K.; Takeyama, Y.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1542-1553. For photochemical oxyperfluoroalkylation reaction of simple alkenes using molecular oxygen, see: (e) Yoshida, M.; Ohkoshi, M.; Aoki, N.; Ohnuma, Y.; Iyoda, M. Tetrahedron Lett. 1999, 40, 5731-5734.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5731-5734
    • Yoshida, M.1    Ohkoshi, M.2    Aoki, N.3    Ohnuma, Y.4    Iyoda, M.5
  • 11
    • 0000813349 scopus 로고
    • and references cited therein
    • For radical-mediated perfluoroalkylation reactions of α-methylene esters, see: (a) Kamigata, N.; Fukushima, T.; Terakawa, Y.; Yoshida, M.; Iyoda, M. J. Chem. Soc., Perkin Trans. 1 1991, 627-633; (b) Qui, Z.-M.; Burton, D. J. J. Org. Chem. 1995, 60, 3465-3472 and references cited therein.
    • (1995) J. Org. Chem. , vol.60 , pp. 3465-3472
    • Qui, Z.-M.1    Burton, D.J.2
  • 18
    • 33845375277 scopus 로고
    • Transformation of alkyl halides to alcohols using aqueous carbonate has been reported
    • Transformation of alkyl halides to alcohols using aqueous carbonate has been reported: (a) Smith, J. G.; Dibble, P. W.; Sandborn, R. E. J. Org. Chem. 1986, 51, 3762-3768; (b) Ji, J.; Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160-1169.
    • (1986) J. Org. Chem. , vol.51 , pp. 3762-3768
    • Smith, J.G.1    Dibble, P.W.2    Sandborn, R.E.3
  • 19
    • 0028945771 scopus 로고
    • Transformation of alkyl halides to alcohols using aqueous carbonate has been reported: (a) Smith, J. G.; Dibble, P. W.; Sandborn, R. E. J. Org. Chem. 1986, 51, 3762-3768; (b) Ji, J.; Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160-1169.
    • (1995) J. Org. Chem. , vol.60 , pp. 1160-1169
    • Ji, J.1    Zhang, C.2    Lu, X.3
  • 20
    • 85031135444 scopus 로고    scopus 로고
    • 3I (gaseous, ca. 6 equiv.) at -30°C. Then the reaction mixture was stirred at rt for 6 h, and filtered through a pad of Celite. The filtrate was concentrated and the residue was chromatographed on silica gel to afford the product.
    • 3I (gaseous, ca. 6 equiv.) at -30°C. Then the reaction mixture was stirred at rt for 6 h, and filtered through a pad of Celite. The filtrate was concentrated and the residue was chromatographed on silica gel to afford the product.
  • 23
    • 85031143294 scopus 로고    scopus 로고
    • 13C NMR with those of 2e.
    • 13C NMR with those of 2e .


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