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Volumn 68, Issue 2, 2003, Pages 625-627

Hydroxyalkylation of α-C-H bonds of tetrahydrofuran with aldehydes in the presence of triethylborane and tert-butyl hydroperoxide

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYALKYLATION;

EID: 0037462347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020590e     Document Type: Article
Times cited : (42)

References (53)
  • 1
    • 0012233552 scopus 로고    scopus 로고
    • Reviews for the C-H activation of organic molecules by metal complexes: (a) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047. (d) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, Germany, 1999. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
    • (1997) Chem. Rev. , vol.97 , pp. 2879
    • Shilov, A.E.1    Shulpin, G.B.2
  • 2
    • 0033553817 scopus 로고    scopus 로고
    • Reviews for the C-H activation of organic molecules by metal complexes: (a) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047. (d) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, Germany, 1999. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1698
    • Dyker, G.1
  • 3
    • 0032783372 scopus 로고    scopus 로고
    • Reviews for the C-H activation of organic molecules by metal complexes: (a) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047. (d) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, Germany, 1999. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
    • (1999) Eur. J. Inorg. Chem. , pp. 1047
    • Guari, Y.1    Sabo-Etienne, S.2    Chaudret, B.3
  • 4
    • 0003464704 scopus 로고    scopus 로고
    • Springer: Berlin, Germany
    • Reviews for the C-H activation of organic molecules by metal complexes: (a) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047. (d) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, Germany, 1999. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
    • (1999) Activation of Unreactive Bonds and Organic Synthesis
    • Murai, S.1
  • 5
    • 0034867872 scopus 로고    scopus 로고
    • Reviews for the C-H activation of organic molecules by metal complexes: (a) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047. (d) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, Germany, 1999. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 633
    • Jia, C.1    Kitamura, T.2    Fujiwara, Y.3
  • 6
    • 0000820085 scopus 로고
    • Reviews for the C-H activation of organic molecules by metal complexes: (a) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047. (d) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, Germany, 1999. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 154
    • Arndtsen, B.A.1    Bergman, R.G.2    Mobley, T.A.3    Peterson, T.H.4
  • 7
    • 0036589261 scopus 로고    scopus 로고
    • Reviews for the C-H activation of organic molecules by metal complexes: (a) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047. (d) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, Germany, 1999. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
    • (2002) Chem. Rev. , vol.102 , pp. 1731
    • Ritleng, V.1    Sirlin, C.2    Pfeffer, M.3
  • 8
    • 0037198618 scopus 로고    scopus 로고
    • Reviews for the C-H activation of organic molecules by metal complexes: (a) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (c) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047. (d) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, Germany, 1999. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (g) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
    • (2002) Nature , vol.417 , pp. 507
    • Labinger, J.A.1    Bercaw, J.E.2
  • 32
    • 33748243464 scopus 로고
    • C-C bond formation at the alkoxy group by transition-metal-promoted C-H activation is also known: (a) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023. (b) Lin, Y.; Ma, D.; Lu, X. Tetrahedron Lett. 1987, 28, 3249. (c) Ohishi, T.; Yamada, J.; Inui, Y.; Sakaguchi, T.; Yamashita, M. J. Org. Chem. 1994, 59, 7521.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 1023
    • Dyker, G.1
  • 33
    • 45949123134 scopus 로고
    • C-C bond formation at the alkoxy group by transition-metal-promoted C-H activation is also known: (a) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023. (b) Lin, Y.; Ma, D.; Lu, X. Tetrahedron Lett. 1987, 28, 3249. (c) Ohishi, T.; Yamada, J.; Inui, Y.; Sakaguchi, T.; Yamashita, M. J. Org. Chem. 1994, 59, 7521.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3249
    • Lin, Y.1    Ma, D.2    Lu, X.3
  • 34
    • 0001005198 scopus 로고
    • C-C bond formation at the alkoxy group by transition-metal-promoted C-H activation is also known: (a) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023. (b) Lin, Y.; Ma, D.; Lu, X. Tetrahedron Lett. 1987, 28, 3249. (c) Ohishi, T.; Yamada, J.; Inui, Y.; Sakaguchi, T.; Yamashita, M. J. Org. Chem. 1994, 59, 7521.
    • (1994) J. Org. Chem. , vol.59 , pp. 7521
    • Ohishi, T.1    Yamada, J.2    Inui, Y.3    Sakaguchi, T.4    Yamashita, M.5
  • 36
    • 0035498332 scopus 로고    scopus 로고
    • Pertinent reviews for organoborane-mediated radical reactions: (a) Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415. (b) Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 2002, 674. (c) Oshima, K.; Utimoto, K. J. Synth. Org. Chem., Jpn. 1989, 40.
    • (2001) Chem. Rev. , vol.101 , pp. 3415
    • Ollivier, C.1    Renaud, P.2
  • 37
    • 0036250217 scopus 로고    scopus 로고
    • Pertinent reviews for organoborane-mediated radical reactions: (a) Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415. (b) Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 2002, 674. (c) Oshima, K.; Utimoto, K. J. Synth. Org. Chem., Jpn. 1989, 40.
    • (2002) Synlett , pp. 674
    • Yorimitsu, H.1    Shinokubo, H.2    Oshima, K.3
  • 38
    • 85007735934 scopus 로고
    • Pertinent reviews for organoborane-mediated radical reactions: (a) Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415. (b) Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 2002, 674. (c) Oshima, K.; Utimoto, K. J. Synth. Org. Chem., Jpn. 1989, 40.
    • (1989) J. Synth. Org. Chem., Jpn. , pp. 40
    • Oshima, K.1    Utimoto, K.2
  • 40
    • 0033036268 scopus 로고    scopus 로고
    • TEMPO(2,2,6,6-tetramethylpiperidin-1-oxyl)-induced generation of alkyl radicals from B-alkylcatecholboranes: Ollivier, C.; Chuard, R.; Renaud, P. Synlett 1999, 807.
    • (1999) Synlett , pp. 807
    • Ollivier, C.1    Chuard, R.2    Renaud, P.3
  • 41
    • 0033166292 scopus 로고    scopus 로고
    • Recent studies on the intramolecular addition of alkyl radicals to carbonyl compounds: (a) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 5511. (b) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833. (c) Chareyron, M.; Devin, P.; Fensterbank, L.; Malacria, M. Synlett 2000, 83. (d) Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429. Review: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5511
    • Devin, P.1    Fensterbank, L.2    Malacria, M.3
  • 42
    • 0032546072 scopus 로고    scopus 로고
    • Recent studies on the intramolecular addition of alkyl radicals to carbonyl compounds: (a) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 5511. (b) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833. (c) Chareyron, M.; Devin, P.; Fensterbank, L.; Malacria, M. Synlett 2000, 83. (d) Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429. Review: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 833
    • Devin, P.1    Fensterbank, L.2    Malacria, M.3
  • 43
    • 0033972361 scopus 로고    scopus 로고
    • Recent studies on the intramolecular addition of alkyl radicals to carbonyl compounds: (a) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 5511. (b) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833. (c) Chareyron, M.; Devin, P.; Fensterbank, L.; Malacria, M. Synlett 2000, 83. (d) Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429. Review: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.
    • (2000) Synlett , pp. 83
    • Chareyron, M.1    Devin, P.2    Fensterbank, L.3    Malacria, M.4
  • 44
    • 37049078160 scopus 로고
    • Recent studies on the intramolecular addition of alkyl radicals to carbonyl compounds: (a) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 5511. (b) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833. (c) Chareyron, M.; Devin, P.; Fensterbank, L.; Malacria, M. Synlett 2000, 83. (d) Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429. Review: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 429
    • Clive, D.L.J.1    Postema, M.H.D.2
  • 45
    • 0042789931 scopus 로고
    • Recent studies on the intramolecular addition of alkyl radicals to carbonyl compounds: (a) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 5511. (b) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833. (c) Chareyron, M.; Devin, P.; Fensterbank, L.; Malacria, M. Synlett 2000, 83. (d) Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429. Review: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.
    • (1993) Chem. Rev. , vol.93 , pp. 2091
    • Dowd, P.1    Zhang, W.2
  • 52
    • 0347611959 scopus 로고    scopus 로고
    • note
    • The tert-butoxy radical possibly generated via the homolysis of TBHP with ethyl radicals is also likely to abstract α-L-C-H bonds of THF to produce THF radical 4.


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