메뉴 건너뛰기




Volumn 40, Issue 9, 2011, Pages 928-930

Copper-catalyzed conjugate additions of alkylboranes to aryl α,β-Unsaturated Ketones

Author keywords

[No Author keywords available]

Indexed keywords


EID: 80052586553     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.928     Document Type: Article
Times cited : (18)

References (45)
  • 1
    • 0035126119 scopus 로고    scopus 로고
    • For reviews on transition-metal-catalyzed conjugate additions see:
    • For reviews on transition-metal-catalyzed conjugate additions, see: N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171.
    • (2001) Synthesis , pp. 171
    • Krause, N.1    Hoffmann-Röder, A.2
  • 6
    • 5244346814 scopus 로고    scopus 로고
    • For selected references on Rh-catalyzed conjugate additions with aryl- and alkenylboron compounds, see:
    • For selected references on Rh-catalyzed conjugate additions with aryl- and alkenylboron compounds, see: M. Sakai, H. Hayashi, N. Miyaura, Organometallics 1997, 16, 4229.
    • (1997) Organometallics , vol.16 , pp. 4229
    • Sakai, M.1    Hayashi, H.2    Miyaura, N.3
  • 11
    • 0028327540 scopus 로고
    • For selected references on Pd-catalyzed conjugate additions with aryl- and alkenylboron compounds, see:
    • For selected references on Pd-catalyzed conjugate additions with aryl- and alkenylboron compounds, see: C. S. Cho, K. Tanabe, S. Uemura, Tetrahedron Lett. 1994, 35, 1275.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 1275
    • Cho, C.S.1    Tanabe, K.2    Uemura, S.3
  • 20
    • 33749315506 scopus 로고    scopus 로고
    • For Ni-catalyzed conjugate additions with arylboron compounds, see:
    • For Ni-catalyzed conjugate additions with arylboron compounds, see: E. Shirakawa, Y. Yasuhara, T. Hayashi, Chem. Lett. 2006, 35, 768.
    • (2006) Chem. Lett. , vol.35 , pp. 768
    • Shirakawa, E.1    Yasuhara, Y.2    Hayashi, T.3
  • 21
    • 33847628731 scopus 로고    scopus 로고
    • For conjugate additions with allylboron compounds, see:
    • For conjugate additions with allylboron compounds, see: J. D. Sieber, S. Liu, J. P. Morken, J. Am. Chem. Soc. 2007, 129, 2214.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 2214
    • Sieber, J.D.1    Liu, S.2    Morken, J.P.3
  • 24
    • 0038030790 scopus 로고
    • For conjugate additions with alkylboron compounds, see:
    • For conjugate additions with alkylboron compounds, see: N. Miyaura, M. Itoh, A. Suzuki, Tetrahedron Lett. 1976, 17, 255.
    • (1976) Tetrahedron Lett. , vol.17 , pp. 255
    • Miyaura, N.1    Itoh, M.2    Suzuki, A.3
  • 26
    • 79952656192 scopus 로고    scopus 로고
    • For a review on transition-metal-catalyzed cross-coupling reactions using alkyl-organometallic reagents, see:
    • For a review on transition-metal-catalyzed cross-coupling reactions using alkyl-organometallic reagents, see: R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417.
    • (2011) Chem. Rev. , vol.111 , pp. 1417
    • Jana, R.1    Pathak, T.P.2    Sigman, M.S.3
  • 28
    • 46749105898 scopus 로고    scopus 로고
    • For Cu-catalyzed conjugate addition of arylboronic acid to alkynoates, see:
    • For Cu-catalyzed conjugate addition of arylboronic acid to alkynoates, see: Y. Yamamoto, N. Kirai, Y. Harada, Chem. Commun. 2008, 2010.
    • (2008) Chem. Commun. , vol.2010
    • Yamamoto, Y.1    Kirai, N.2    Harada, Y.3
  • 29
    • 77949357065 scopus 로고    scopus 로고
    • For Cu-catalyzed γ-selective and stereospecific allylalkyl and allylaryl couplings with organoboron compounds, see:
    • For Cu-catalyzed γ-selective and stereospecific allylalkyl and allylaryl couplings with organoboron compounds, see: H. Ohmiya, U. Yokobori, Y. Makida, M. Sawamura, J. Am. Chem. Soc. 2010, 132, 2895.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2895
    • Ohmiya, H.1    Yokobori, U.2    Makida, Y.3    Sawamura, M.4
  • 32
    • 79952120576 scopus 로고    scopus 로고
    • For Cu-catalyzed carboxylations with alkylboron compounds (alkyl-9-BBN) to carbon dioxide, see:
    • H. Ohmiya, M. Tanabe, M. Sawamura, Org. Lett. 2011, 13, 1086.
    • (2011) Org. Lett. , vol.13 , pp. 1086
    • Ohmiya, H.1    Tanabe, M.2    Sawamura, M.3
  • 33
    • 0000929712 scopus 로고    scopus 로고
    • Knochel et al. reported the copper-mediated conjugate addition of dialkylzinc reagents, prepared by a hydroboration/ boronzinc exchange sequence, to ethyl acrylate, but the application to β-substituted α,β-unsaturated esters is underdeveloped while benzylidene malonate has successfully been used. Furthermore, the cumbersome procedure and low atom efficiency, using large excess substrate and reagents, hampers the wide application of this method. See:
    • Knochel et al. reported the copper-mediated conjugate addition of dialkylzinc reagents, prepared by a hydroboration/ boronzinc exchange sequence, to ethyl acrylate, but the application to β-substituted α,β-unsaturated esters is underdeveloped while benzylidene malonate has successfully been used. Furthermore, the cumbersome procedure and low atom efficiency, using large excess substrate and reagents, hampers the wide application of this method. See: F. Langer, L. Schwink, A. Devasagayaraj, P.-Y. Chavant, P. Knochel, J. Org. Chem. 1996, 61, 8229.
    • (1996) J. Org. Chem. , vol.61 , pp. 8229
    • Langer, F.1    Schwink, L.2    Devasagayaraj, A.3    Chavant, P.-Y.4    Knochel, P.5
  • 37
    • 33744926164 scopus 로고    scopus 로고
    • For selected references on Cu-catalyzed enantioselective conjugate additions with alkylmagnesium- or alkylzinc reagents, see:
    • For selected references on Cu-catalyzed enantioselective conjugate additions with alkylmagnesium- or alkylzinc reagents, see: K.-s. Lee, M. K. Brown, A. W. Hird, A. H. Hoveyda, J. Am. Chem. Soc. 2006, 128, 7182.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 7182
    • Lee, K.-S.1    Brown, M.K.2    Hird, A.W.3    Hoveyda, A.H.4
  • 41
    • 33745688099 scopus 로고    scopus 로고
    • IPr: 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene; SIPr: 1,3-Bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene; IMes: 1,3-Bis(2,4,6- trimethylphenyl)imidazol-2-ylidene; ICy: 1,3-Dicyclohexylimidazol-2-ylidene; For reviews on N-heterocyclic carbenes (NHCs), see: Springer, Heidelberg, doi:10.1007/978-3-540-36930-1
    • IPr: 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene; SIPr: 1,3-Bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene; IMes: 1,3-Bis(2,4,6- trimethylphenyl)imidazol-2-ylidene; ICy: 1,3-Dicyclohexylimidazol-2-ylidene; For reviews on N-heterocyclic carbenes (NHCs), see: N-Heterocyclic Carbenes in Transition Metal Catalysis in Topics in Organometallic Chemistry, ed. by F. Glorius, Springer, Heidelberg, 2007, Vol. 21. doi:10.1007/978-3-540-36930-1
    • (2007) N-Heterocyclic Carbenes in Transition Metal Catalysis in Topics in Organometallic Chemistry , vol.21
    • Glorius, F.1
  • 45
    • 0000915956 scopus 로고
    • The reaction between 2a and 3a in the presence of the radical inhibitor, TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl) under otherwise identical conditions afforded 3aa in 83% yield. Thus, the radical mechanism should be ruled out. For a conjugate addition of trialkylboranes to α,β- unsaturated aldehydes and ketones under radical conditions, see:
    • The reaction between 2a and 3a in the presence of the radical inhibitor, TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl) under otherwise identical conditions afforded 3aa in 83% yield. Thus, the radical mechanism should be ruled out. For a conjugate addition of trialkylboranes to α,β- unsaturated aldehydes and ketones under radical conditions, see: H. C. Brown, G. W. Kabalka, J. Am. Chem. Soc. 1970, 92, 714.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 714
    • Brown, H.C.1    Kabalka, G.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.