메뉴 건너뛰기




Volumn 43, Issue 14, 2004, Pages 1871-1876

A rationally designed universal catalyst for Suzuki-Miyaura coupling processes

Author keywords

Aryl chlorides; Boronic acids; Cross coupling; Palladium; Phosphane ligands

Indexed keywords

CATALYSTS; CHLORIDE MINERALS; SYNTHESIS (CHEMICAL); TEMPERATURE CONTROL;

EID: 3042654141     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353615     Document Type: Article
Times cited : (839)

References (39)
  • 4
    • 1642580702 scopus 로고    scopus 로고
    • The majority of the examples demonstrating high turnover numbers for the coupling reactions of unactivated substrates use phenyl boronic acid as the coupling partner. However, success with this substrate rarely translates into similiar levels of activity or generality with even slightly more hindered or functionalized substrates. For recent examples of cross-couplings employing phenylboronic acid see: a) A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dingerdissen, M. Beller, Chem. Commun. 2004, 1, 38;
    • (2004) Chem. Commun. , vol.1 , pp. 38
    • Zapf, A.1    Jackstell, R.2    Rataboul, F.3    Riermeier, T.4    Monsees, A.5    Fuhrmann, C.6    Shaikh, N.7    Dingerdissen, U.8    Beller, M.9
  • 6
    • 0037471219 scopus 로고    scopus 로고
    • b) N. Leadbeater, M. Marco, Angew. Chem. 2003, 115, 1445; Angew. Chem. Int. Ed. 2003, 42, 1407;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1407
  • 9
    • 0037122141 scopus 로고    scopus 로고
    • d) J. P. Stambuli, R. Kuwano, J. F. Hartwig, Angew. Chem. 2002, 114, 940; Angew. Chem. Int. Ed. 2002, 41, 4746;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4746
  • 11
    • 0034680642 scopus 로고    scopus 로고
    • e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2009, 112, 4315; Angew. Chem. Int. Ed. 2000, 39, 4153.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4153
  • 15
    • 0042728760 scopus 로고
    • For a review see: A. D. Ryabov, Chem. Rev. 1990, 90, 403.
    • (1990) Chem. Rev. , vol.90 , pp. 403
    • Ryabov, A.D.1
  • 20
    • 0036432935 scopus 로고    scopus 로고
    • b) R. B. Bedford, S. L. Hazelwood, M. E. Limmert, Chem. Commun. 2002, 2610. The presence of underligated Pd complexes may promote the formation of Pd black. For a recent study on the deactivation processes of homogeneous Pd catalysts see: M. Tromp, J. R. A. Sietsma, J. A. van Bokhoven, G. P. F. van Strijdonck, R. J. van Haaren, A. M. J. van der Eerden, P. W. N. M. van Leeuwen, D. C. Koningsberger, Chem. Commun. 2003, 128.
    • (2002) Chem. Commun. , pp. 2610
    • Bedford, R.B.1    Hazelwood, S.L.2    Limmert, M.E.3
  • 22
    • 0013319981 scopus 로고    scopus 로고
    • For a review on Pd-catalyzed couplings of aryl chlorides see: A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350; Angew. Chem. Int. Ed. 2002, 41, 4176.
    • (2002) Angew. Chem. , vol.114 , pp. 4350
    • Littke, A.F.1    Fu, G.C.2
  • 23
    • 0037112673 scopus 로고    scopus 로고
    • For a review on Pd-catalyzed couplings of aryl chlorides see: A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350; Angew. Chem. Int. Ed. 2002, 41, 4176.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4176
  • 27
    • 0042969355 scopus 로고    scopus 로고
    • c) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818; Angew. Chem. Int. Ed. 2003, 42, 3690;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3690
  • 29
    • 4544250109 scopus 로고    scopus 로고
    • note
    • e) The best previous results for this reaction are described in ref. [2c], although no yield of isolated product is reported.
  • 30
    • 4544283518 scopus 로고    scopus 로고
    • note
    • The half-life was determined by GC analysis.
  • 31
    • 4544314700 scopus 로고    scopus 로고
    • note
    • While exceedingly high turnover numbers have been realized for the coupling of phenyl boronic acid with 4-bromoacetophenone, this is a particularly trivial process and does not extend to the efficient coupling of unactivated and ortho-substituted substrates at low catalyst levels. We have previously shown this reaction to proceed even in the absence of added ligand and recommend that it not be used as a benchmark to test new catalysts, see ref. [7a].
  • 32
    • 0037047555 scopus 로고    scopus 로고
    • For a recent report describing the cross-coupling of aryl chlorides with alkyl boronic acids, see: N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553. For a report describing the coupling of an alkyl boronic acid with an alkyl bromide, see: J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662.
    • (2002) J. Org. Chem. , vol.67 , pp. 5553
    • Kataoka, N.1    Shelby, Q.2    Stambuli, J.P.3    Hartwig, J.F.4
  • 33
    • 0037146031 scopus 로고    scopus 로고
    • For a recent report describing the cross-coupling of aryl chlorides with alkyl boronic acids, see: N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553. For a report describing the coupling of an alkyl boronic acid with an alkyl bromide, see: J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 13662
    • Kirchhoff, J.H.1    Netherton, M.R.2    Hills, I.D.3    Fu, G.C.4
  • 34
    • 0004150157 scopus 로고    scopus 로고
    • G. M. Sheldrick, University of Göttingen, and Siemens Industrial Automation, Inc.
    • -3. CCDC-227390 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+ 44) 1223-336-033; or deposit@ccdc.carn.ac. uk).
    • SHELXTL V6.10
  • 39
    • 4544313744 scopus 로고    scopus 로고
    • note
    • II palladate species.[14a] While we cannot unequivocally rule this out, the fact that higher levels of catalytic activity for analogous C-N couplings have been observed for catalysts derived from 2-dicyclohexylphosphanyl-2′,4′,6′- triisopropylbiphenyl than for 1 (E. R. Stricter, S. L. Buchwald, unpublished results) cast doubt on this explanation of the high level of catalytic activity manifested with 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.