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Volumn 61, Issue 41, 2005, Pages 9860-9868

Aryl alkynylation versus alkyne homocoupling: Unprecedented selectivity switch in Cu, phosphine and solvent-free heterogeneous Pd-catalysed couplings

Author keywords

C C coupling; Heterogeneous catalysis; Kinetics; N ligands; Palladium

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE DERIVATIVE; COPPER; IODOBENZENE; LIGAND; ORGANIC SOLVENT; PALLADIUM COMPLEX; PHOSPHINE; PHOSPHORUS DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILICA GEL; SOLVENT;

EID: 24344450316     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.082     Document Type: Article
Times cited : (100)

References (69)
  • 32
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    • Examples of solely nitrogen containing ligands are quite rare in heterogeneously catalysed cross-couplings: see Ref. 14a-c. For a comprehensive review on the metallo-aza ligand complexes see: (a) A. Togni, and L.M. Venanzi Angew. Chem., Int. Ed. Engl. 33 1994 497 526
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 497-526
    • Togni, A.1    Venanzi, L.M.2
  • 38
    • 4043066278 scopus 로고    scopus 로고
    • For recent example of ligand, copper and amine-free homogeneous Sonogashira reaction see: S. Urgaonkar, and J.G. Verkade J. Org. Chem. 69 2004 5752 5755
    • (2004) J. Org. Chem. , vol.69 , pp. 5752-5755
    • Urgaonkar, S.1    Verkade, J.G.2
  • 48
    • 24344454070 scopus 로고    scopus 로고
    • note
    • The use of bromo derivatives such as 4-bromobenzonitrile and 4-bromoacetophenone required the use of catalytic amounts of CuI (5 mol%) in order to obtain synthetically useful yields (92 and 69%, respectively, hetero:homo >50:1).
  • 49
    • 24344468932 scopus 로고    scopus 로고
    • note
    • 4.
  • 51
    • 24344466048 scopus 로고    scopus 로고
    • note
    • As soon as the Pd-catalyst was added to the reaction mixture the common deep red colour of the [Pd(0)]-alkyne complexes appeared.
  • 52
    • 33947476790 scopus 로고
    • For representative examples of homocoupling procedures of terminal alkynes to diynes in the presence of stoichiometric palladium based oxidants see: (a) A.S. Hay J. Org. Chem. 27 1962 3320 3321
    • (1962) J. Org. Chem. , vol.27 , pp. 3320-3321
    • Hay, A.S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.