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Volumn 61, Issue 41, 2005, Pages 9878-9885

A simple catalyst system for the palladium-catalyzed coupling of aryl halides with terminal alkynes

Author keywords

Alkynes; Aryl halides; Coupling reactions; Palladium and compounds

Indexed keywords

ALKYNE; DIMETHYL SULFOXIDE; HALIDE; PALLADIUM; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM DIHYDROGEN PHOSPHATE; TRIPHENYLPHOSPHINE;

EID: 24344485170     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.099     Document Type: Article
Times cited : (48)

References (84)
  • 4
    • 0003995267 scopus 로고    scopus 로고
    • E. Negishi Wiley-Interscience New York
    • The palladium-catalyzed coupling of aryl and alkenyl halides with alkynylmetals is an effective alternative. For a recent review, see: E. Negishi, and C. Xu E. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis 2002 Wiley-Interscience New York 531 549 See also Ref. 1c
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , pp. 531-549
    • Negishi, E.1    Xu, C.2
  • 16
    • 0033750821 scopus 로고    scopus 로고
    • For a review, see: (C) U.H.F. Bunz Chem. Rev. 100 2000 1605 1644
    • (2000) Chem. Rev. , vol.100 , pp. 1605-1644
    • Bunz, U.H.F.1
  • 21
    • 24344464696 scopus 로고    scopus 로고
    • Heck and co-workers had already reported the coupling reaction in piperidine at 100°C but they did not mention its efficiency. See Ref. 6.
    • Heck and co-workers had already reported the coupling reaction in piperidine at 100°C but they did not mention its efficiency. See Ref. 6.
  • 56
    • 15444371592 scopus 로고    scopus 로고
    • 2O as a solvent, unfortunately the scope is narrow, where only electron-deficient aryl iodides coupled with phenylacetylene or 3-butyn-1-ol in acceptable yields. G. Zhang Synlett 2005 619 622
    • (2005) Synlett , pp. 619-622
    • Zhang, G.1
  • 57
    • 24344510665 scopus 로고    scopus 로고
    • note
    • 3, is used effectively in combination with a special media (Ref. 12b) or a special ligand (Refs. 13i and 13l).
  • 58
    • 24344499601 scopus 로고    scopus 로고
    • note
    • To the best of our knowledge, potassium phosphate, one of the most popular bases for the Suzuki-Miyaura coupling reaction, has hardly been used in the Sonogashira coupling and the copper-free version of the reaction.
  • 59
    • 0035944139 scopus 로고    scopus 로고
    • To the best of our knowledge, use of DMSO as a solvent in the palladium-catalyzed coupling reaction of terminal alkynes has only one precedent, where the reaction of an alkyne with a 2-aryl-1,1-dibromoethene gave a diyne by the Sonogashira coupling reaction accompanied by dehydrobromination. H.B. Lee, D.H. Huh, J.S. Oh, G.-H. Min, B.H. Kim, D.H. Lee, J.K. Hwang, and Y.G. Kim Tetrahedron 57 2001 8283 8290
    • (2001) Tetrahedron , vol.57 , pp. 8283-8290
    • Lee, H.B.1    Huh, D.H.2    Oh, J.S.3    Min, G.-H.4    Kim, B.H.5    Lee, D.H.6    Hwang, J.K.7    Kim, Y.G.8
  • 60
    • 24344479416 scopus 로고    scopus 로고
    • note
    • 3 in an aromatic solvent such as toluene and benzene.
  • 61
    • 0030903044 scopus 로고    scopus 로고
    • IP as well as other iminophosphine ligands are reported to be a excellent ligand in the following palladium-catalyzed coupling reaction of organostannanes. Cross-coupling reaction with aryl halides: (a) E. Shirakawa, H. Yoshida, and H. Takaya Tetrahedron Lett. 38 1997 3759 3762
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3759-3762
    • Shirakawa, E.1    Yoshida, H.2    Takaya, H.3
  • 67
    • 24344489687 scopus 로고    scopus 로고
    • Available from Aldrich Chemical Co.
    • Available from Aldrich Chemical Co.
  • 68
    • 24344477991 scopus 로고    scopus 로고
    • note
    • 4 at the beginning and 1.2 equiv after 24 h.
  • 69
    • 84988204469 scopus 로고
    • One-pot procedures with the aid of a copper catalyst have already been developed. (a) A. Carpita, A. Lessi, and R. Rossi Synthesis 1984 571 572
    • (1984) Synthesis , pp. 571-572
    • Carpita, A.1    Lessi, A.2    Rossi, R.3
  • 73
    • 0028329356 scopus 로고
    • In the palladium-catalyzed coupling reaction of aryl halides, aryl groups of triarylphosphine ligands instead of that of the aryl halides sometimes undergo the coupling with nucleophiles through exchange of substituents between palladium and phosphorous atoms. For example, see: (a) G.T. Crisp, and P.T. Glink Tetrahedron 50 1994 3213 3234
    • (1994) Tetrahedron , vol.50 , pp. 3213-3234
    • Crisp, G.T.1    Glink, P.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.