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Volumn 121, Issue 28, 1999, Pages 6607-6615

Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE DERIVATIVE; ORGANIC SOLVENT; RADICAL; REAGENT; TIN DERIVATIVE;

EID: 0033591868     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990069a     Document Type: Article
Times cited : (154)

References (82)
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    • Tin hydrides: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Horner, J. H.; Martinez, F. N.; Newcomb, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 2783. (c) Hadida, S.; Super, M. S.; Beckman, E. J.; Curran, D. P. J. Am. Chem. Soc. 1997, 119, 7406. (d) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883.
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    • Other tin chemistry: (a) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480. (b) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (c) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Spetseris, N.; Hadida, S.; Curran, D. P.; Meyer, T. Y. Organometallics 1998, 17, 1458. (f) Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261. (g) Curran, D. P.; Luo, Z.; Degenkolb, P. Biorg. Med Chem. Lett. 1998, 8, 2403. (h) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett., in press.
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    • Other tin chemistry: (a) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480. (b) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (c) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Spetseris, N.; Hadida, S.; Curran, D. P.; Meyer, T. Y. Organometallics 1998, 17, 1458. (f) Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261. (g) Curran, D. P.; Luo, Z.; Degenkolb, P. Biorg. Med Chem. Lett. 1998, 8, 2403. (h) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett., in press.
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    • Other tin chemistry: (a) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480. (b) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (c) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Spetseris, N.; Hadida, S.; Curran, D. P.; Meyer, T. Y. Organometallics 1998, 17, 1458. (f) Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261. (g) Curran, D. P.; Luo, Z.; Degenkolb, P. Biorg. Med Chem. Lett. 1998, 8, 2403. (h) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett., in press.
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    • Curran, D.P.1    Hadida, S.2    He, M.3
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    • Other tin chemistry: (a) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480. (b) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (c) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Spetseris, N.; Hadida, S.; Curran, D. P.; Meyer, T. Y. Organometallics 1998, 17, 1458. (f) Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261. (g) Curran, D. P.; Luo, Z.; Degenkolb, P. Biorg. Med Chem. Lett. 1998, 8, 2403. (h) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett., in press.
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    • Hoshino, M.1    Degenkolb, P.2    Curran, D.P.3
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    • Other tin chemistry: (a) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480. (b) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (c) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Spetseris, N.; Hadida, S.; Curran, D. P.; Meyer, T. Y. Organometallics 1998, 17, 1458. (f) Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261. (g) Curran, D. P.; Luo, Z.; Degenkolb, P. Biorg. Med Chem. Lett. 1998, 8, 2403. (h) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett., in press.
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    • Other tin chemistry: (a) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480. (b) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (c) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Spetseris, N.; Hadida, S.; Curran, D. P.; Meyer, T. Y. Organometallics 1998, 17, 1458. (f) Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261. (g) Curran, D. P.; Luo, Z.; Degenkolb, P. Biorg. Med Chem. Lett. 1998, 8, 2403. (h) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett., in press.
    • (1998) Med. Chem. Res. , vol.8 , pp. 261
    • Curran, D.P.1    Luo, Z.2
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    • Other tin chemistry: (a) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480. (b) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (c) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Spetseris, N.; Hadida, S.; Curran, D. P.; Meyer, T. Y. Organometallics 1998, 17, 1458. (f) Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261. (g) Curran, D. P.; Luo, Z.; Degenkolb, P. Biorg. Med Chem. Lett. 1998, 8, 2403. (h) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett., in press.
    • (1998) Biorg. Med Chem. Lett. , vol.8 , pp. 2403
    • Curran, D.P.1    Luo, Z.2    Degenkolb, P.3
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    • in press
    • Other tin chemistry: (a) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480. (b) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (c) Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Spetseris, N.; Hadida, S.; Curran, D. P.; Meyer, T. Y. Organometallics 1998, 17, 1458. (f) Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261. (g) Curran, D. P.; Luo, Z.; Degenkolb, P. Biorg. Med Chem. Lett. 1998, 8, 2403. (h) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett., in press.
    • Tetrahedron Lett.
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    • "Fluorous synthesis" techniques: (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (b) Studer, A.; Curran, D. P. Tetrahedron 1997, 53, 6681. (c) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917. (d) Curran, D. P.; Ferritto, R.; Hua, Y. Tetrahedron Lett. 1998, 39, 4937. (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (f) Lindau, B.; Singh, A.; Curran, D. P. J. Org. Chem., in press.
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    • "Fluorous synthesis" techniques: (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (b) Studer, A.; Curran, D. P. Tetrahedron 1997, 53, 6681. (c) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917. (d) Curran, D. P.; Ferritto, R.; Hua, Y. Tetrahedron Lett. 1998, 39, 4937. (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (f) Lindau, B.; Singh, A.; Curran, D. P. J. Org. Chem., in press.
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    • Studer, A.1    Jeger, P.2    Wipf, P.3    Curran, D.P.4
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    • 0032500101 scopus 로고    scopus 로고
    • "Fluorous synthesis" techniques: (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (b) Studer, A.; Curran, D. P. Tetrahedron 1997, 53, 6681. (c) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917. (d) Curran, D. P.; Ferritto, R.; Hua, Y. Tetrahedron Lett. 1998, 39, 4937. (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (f) Lindau, B.; Singh, A.; Curran, D. P. J. Org. Chem., in press.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4937
    • Curran, D.P.1    Ferritto, R.2    Hua, Y.3
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    • "Fluorous synthesis" techniques: (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (b) Studer, A.; Curran, D. P. Tetrahedron 1997, 53, 6681. (c) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917. (d) Curran, D. P.; Ferritto, R.; Hua, Y. Tetrahedron Lett. 1998, 39, 4937. (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (f) Lindau, B.; Singh, A.; Curran, D. P. J. Org. Chem., in press.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8691
    • Takeuchi, S.1    Nakamura, Y.2    Ohgo, Y.3    Curran, D.P.4
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    • in press
    • "Fluorous synthesis" techniques: (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (b) Studer, A.; Curran, D. P. Tetrahedron 1997, 53, 6681. (c) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917. (d) Curran, D. P.; Ferritto, R.; Hua, Y. Tetrahedron Lett. 1998, 39, 4937. (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (f) Lindau, B.; Singh, A.; Curran, D. P. J. Org. Chem., in press.
    • J. Org. Chem.
    • Lindau, B.1    Singh, A.2    Curran, D.P.3
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    • note
    • "Introducing OXSOL2000" Oxychem Specialty Business Group No. BCG-OX-37, 5/96. Available from Occidental Chemical Corporation. See also Material Safety Data Sheet (MSDS) M35459.


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