메뉴 건너뛰기




Volumn 69, Issue 10, 2004, Pages 3554-3557

Copper-Mediated, Palladium-Catalyzed Coupling of Thiol Esters with Aliphatic Organoboron Reagents

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; COPPER COMPOUNDS; DERIVATIVES; ESTERS; KETONES; OPTIMIZATION; PALLADIUM COMPOUNDS;

EID: 2442510937     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049964p     Document Type: Article
Times cited : (142)

References (39)
  • 2
    • 0037149673 scopus 로고    scopus 로고
    • (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979; Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3 (1), 91; Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3 (14), 2149. Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4 (6), 979. Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4 (6), 983. Liebeskind, L. S.; Srogl, J.; Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74 (1), 115. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweizer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5 (23), 4349.
    • (2002) Org. Lett. , vol.4 , pp. 979
    • Liebeskind, L.S.1    Srogl, J.2
  • 3
    • 0035843313 scopus 로고    scopus 로고
    • (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979; Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3 (1), 91; Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3 (14), 2149. Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4 (6), 979. Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4 (6), 983. Liebeskind, L. S.; Srogl, J.; Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74 (1), 115. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweizer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5 (23), 4349.
    • (2001) Org. Lett. , vol.3 , Issue.1 , pp. 91
    • Savarin, C.1    Srogl, J.2    Liebeskind, L.S.3
  • 4
    • 0035850279 scopus 로고    scopus 로고
    • (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979; Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3 (1), 91; Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3 (14), 2149. Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4 (6), 979. Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4 (6), 983. Liebeskind, L. S.; Srogl, J.; Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74 (1), 115. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweizer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5 (23), 4349.
    • (2001) Org. Lett. , vol.3 , Issue.14 , pp. 2149
    • Savarin, C.1    Liebeskind, L.S.2
  • 5
    • 0037149673 scopus 로고    scopus 로고
    • (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979; Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3 (1), 91; Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3 (14), 2149. Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4 (6), 979. Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4 (6), 983. Liebeskind, L. S.; Srogl, J.; Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74 (1), 115. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweizer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5 (23), 4349.
    • (2002) Org. Lett. , vol.4 , Issue.6 , pp. 979
    • Srogl, J.1    Liebeskind, L.S.2
  • 6
    • 0012215670 scopus 로고    scopus 로고
    • (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979; Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3 (1), 91; Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3 (14), 2149. Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4 (6), 979. Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4 (6), 983. Liebeskind, L. S.; Srogl, J.; Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74 (1), 115. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweizer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5 (23), 4349.
    • (2002) Org. Lett. , vol.4 , Issue.6 , pp. 983
    • Kusturin, C.L.1    Liebeskind, L.S.2    Neumann, W.L.3
  • 7
    • 0036291486 scopus 로고    scopus 로고
    • (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979; Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3 (1), 91; Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3 (14), 2149. Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4 (6), 979. Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4 (6), 983. Liebeskind, L. S.; Srogl, J.; Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74 (1), 115. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweizer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5 (23), 4349.
    • (2002) Pure Appl. Chem. , vol.74 , Issue.1 , pp. 115
    • Liebeskind, L.S.1    Srogl, J.2    Savarin, C.3    Polanco, C.4
  • 8
    • 0344496816 scopus 로고    scopus 로고
    • (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979; Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3 (1), 91; Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3 (14), 2149. Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4 (6), 979. Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4 (6), 983. Liebeskind, L. S.; Srogl, J.; Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74 (1), 115. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweizer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5 (23), 4349.
    • (2003) Org. Lett. , vol.5 , Issue.23 , pp. 4349
    • Kusturin, C.1    Liebeskind, L.S.2    Rahman, H.3    Sample, K.4    Schweizer, B.5    Srogl, J.6    Neumann, W.L.7
  • 9
    • 0141855415 scopus 로고    scopus 로고
    • Egi, M.; Wittenberg, R.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033-3035. Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 801. Alphonse, F.-A. ; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803.
    • (2003) Org. Lett. , vol.5 , pp. 3033-3035
    • Egi, M.1    Wittenberg, R.2    Srogl, J.3    Liebeskind, L.S.4
  • 10
    • 0038204483 scopus 로고    scopus 로고
    • Egi, M.; Wittenberg, R.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033-3035. Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 801. Alphonse, F.-A. ; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803.
    • (2003) Org. Lett. , vol.5 , pp. 801
    • Egi, M.1    Liebeskind, L.S.2
  • 14
    • 37049112962 scopus 로고
    • (b) Kim, S.; Lee, J. I. J. Chem. Soc., Chem. Commun. 1981, 1231), 1-alkynyltrimethysilanes (Kawanami, Y.; Katsuki, I.; Yamaguchi, M. Tetrahedron Lett. 1983, 24, 5131), and organozinc reagents (Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189). Heteroaromatic thioethers participate in a palladium-catalyzed coupling with organozinc reagents (Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett. 2000, 905-907).
    • (1981) J. Chem. Soc., Chem. Commun. , pp. 1231
    • Kim, S.1    Lee, J.I.2
  • 15
    • 0007235777 scopus 로고
    • (b) Kim, S.; Lee, J. I. J. Chem. Soc., Chem. Commun. 1981, 1231), 1-alkynyltrimethysilanes (Kawanami, Y.; Katsuki, I.; Yamaguchi, M. Tetrahedron Lett. 1983, 24, 5131), and organozinc reagents (Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189). Heteroaromatic thioethers participate in a palladium-catalyzed coupling with organozinc reagents (Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett. 2000, 905-907).
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5131
    • Kawanami, Y.1    Katsuki, I.2    Yamaguchi, M.3
  • 16
    • 0032516391 scopus 로고    scopus 로고
    • (b) Kim, S.; Lee, J. I. J. Chem. Soc., Chem. Commun. 1981, 1231), 1-alkynyltrimethysilanes (Kawanami, Y.; Katsuki, I.; Yamaguchi, M. Tetrahedron Lett. 1983, 24, 5131), and organozinc reagents (Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189). Heteroaromatic thioethers participate in a palladium-catalyzed coupling with organozinc reagents (Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett. 2000, 905-907).
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3189
    • Tokuyama, H.1    Yokoshima, S.2    Yamashita, T.3    Fukuyama, T.4
  • 17
    • 0034042632 scopus 로고    scopus 로고
    • (b) Kim, S.; Lee, J. I. J. Chem. Soc., Chem. Commun. 1981, 1231), 1-alkynyltrimethysilanes (Kawanami, Y.; Katsuki, I.; Yamaguchi, M. Tetrahedron Lett. 1983, 24, 5131), and organozinc reagents (Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189). Heteroaromatic thioethers participate in a palladium-catalyzed coupling with organozinc reagents (Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett. 2000, 905-907).
    • (2000) Synlett , pp. 905-907
    • Angiolelli, M.E.1    Casalnuovo, A.L.2    Selby, T.P.3
  • 21
    • 0035903581 scopus 로고    scopus 로고
    • Kakino, R.; Yasumi, S.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc., Jpn. 2002, 75, 137-148. Goossen, L. J.; Ghosh, K. Angew. Chem., Int. Ed. 2001, 40, 3458-3460.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3458-3460
    • Goossen, L.J.1    Ghosh, K.2
  • 27
    • 0025824274 scopus 로고
    • Uemura, M.; Nishimura, H.; Minami, T.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 5402. Rivera, I.; Colberg, J. C.; Soderquist, J. A. Tetrahedron Lett. 1992, 33, 6919. Bhagwat, S. S.; Gude, C.; Cohen, D. S.; Dotson, R.; Mathis, J. ; Lee, W.; Furness, P. J. Med. Chem. 1993, 36, 205. Netherton, M. R.; Dai, C.; Neuschuetz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5402
    • Uemura, M.1    Nishimura, H.2    Minami, T.3    Hayashi, T.4
  • 28
    • 0026439936 scopus 로고
    • Uemura, M.; Nishimura, H.; Minami, T.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 5402. Rivera, I.; Colberg, J. C.; Soderquist, J. A. Tetrahedron Lett. 1992, 33, 6919. Bhagwat, S. S.; Gude, C.; Cohen, D. S.; Dotson, R.; Mathis, J. ; Lee, W.; Furness, P. J. Med. Chem. 1993, 36, 205. Netherton, M. R.; Dai, C.; Neuschuetz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6919
    • Rivera, I.1    Colberg, J.C.2    Soderquist, J.A.3
  • 29
    • 0027474523 scopus 로고
    • Uemura, M.; Nishimura, H.; Minami, T.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 5402. Rivera, I.; Colberg, J. C.; Soderquist, J. A. Tetrahedron Lett. 1992, 33, 6919. Bhagwat, S. S.; Gude, C.; Cohen, D. S.; Dotson, R.; Mathis, J. ; Lee, W.; Furness, P. J. Med. Chem. 1993, 36, 205. Netherton, M. R.; Dai, C.; Neuschuetz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
    • (1993) J. Med. Chem. , vol.36 , pp. 205
    • Bhagwat, S.S.1    Gude, C.2    Cohen, D.S.3    Dotson, R.4    Mathis, J.5    Lee, W.6    Furness, P.7
  • 30
    • 0035904470 scopus 로고    scopus 로고
    • Uemura, M.; Nishimura, H.; Minami, T.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 5402. Rivera, I.; Colberg, J. C.; Soderquist, J. A. Tetrahedron Lett. 1992, 33, 6919. Bhagwat, S. S.; Gude, C.; Cohen, D. S.; Dotson, R.; Mathis, J. ; Lee, W.; Furness, P. J. Med. Chem. 1993, 36, 205. Netherton, M. R.; Dai, C.; Neuschuetz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10099
    • Netherton, M.R.1    Dai, C.2    Neuschuetz, K.3    Fu, G.C.4
  • 38
    • 2442527430 scopus 로고    scopus 로고
    • note
    • Control experiments showed that heating B-undecyl-9-BBN with 1 equiv of CuTC in THF for 3 h produced undecane as the protodeborylation product in more than 90% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.