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Volumn 251, Issue 15-16, 2007, Pages 2017-2055

Performances of symmetrical achiral ferrocenylphosphine ligands in palladium-catalyzed cross-coupling reactions: A review of syntheses, catalytic applications and structural properties

Author keywords

Catalysis; Cross coupling (Heck, Suzuki, Kumada, Negishi, Sonogashira, cyanations, aminations, etherations); Ferrocenylphosphine; Mechanisms (bite angle, conformation, multidentarity); Palladium; Structure

Indexed keywords


EID: 34547775774     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2007.03.020     Document Type: Review
Times cited : (168)

References (196)
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    • See for instance
  • 12
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    • We considered herein ferrocenic monophosphines as "unsymmetrical" species, due to the two different Cp rings. These species have demonstrated some interesting applications reviewed in Ref. [7]; however, their chemistry is not reviewed in the present paper since their syntheses is often tedious, and the contamination with disubstituted by-products very difficult to separate can be unavoidable, see
  • 17
    • 34547814184 scopus 로고    scopus 로고
    • it is worth noting that the product was mentioned at an early stage
  • 22
    • 34547757950 scopus 로고    scopus 로고
    • J.D. Unruh, US Patent, Appl. 822,859 (1977).
  • 42
    • 34547728659 scopus 로고    scopus 로고
    • Kinetics studies have also been reported on Pd/ddpf/alkene complexes, see Ref. [162].
  • 52
    • 2042507954 scopus 로고
    • some examples of the use of Pd/dppf systems as catalysts are mentioned in this review
    • Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457 some examples of the use of Pd/dppf systems as catalysts are mentioned in this review
    • (1995) Chem. Rev. , vol.95 , pp. 2457
    • Miyaura, N.1    Suzuki, A.2
  • 61
    • 34547726216 scopus 로고    scopus 로고
    • 2 has been found sometimes more active to produce 3-substituted propionaldehyde from aryl halides and a boronic acetal, see
  • 115
    • 34547813654 scopus 로고    scopus 로고
    • 2(dppf) nor (dppf)Pd(0) were found to catalyze the cross-coupling of alkyl halides with Grignard reagents, instead the reduction of alkyl electrophiles was observed, see.
  • 124
    • 34547778940 scopus 로고    scopus 로고
    • See Section 3.2.1 for Suzuki coupling and Ref. [47] for details.
  • 134
    • 34547765401 scopus 로고
    • For seminal studies see also;
    • For seminal studies see also;. Cassar L. J. Organomet. Chem. C 57 (1973) 54
    • (1973) J. Organomet. Chem. C , vol.57 , pp. 54
    • Cassar, L.1
  • 178
    • 34547745425 scopus 로고    scopus 로고
    • This is discussed in a relevant review where are distinguished steric bite angle effect and electronic bite angle effect, see
  • 180
    • 34547725696 scopus 로고    scopus 로고
    • Details on "bite angle" definitions are reviewed, see
  • 182
    • 34547727782 scopus 로고    scopus 로고
    • Contradictory reports on bite angle effect on oxidative addition have been reported, which highlight also the influence of Pd/L concentration, see
  • 187
    • 34547740059 scopus 로고    scopus 로고
    • Appendix of Ref. [4] gives a useful compilation of Tolman electronic χ-parameters.
  • 190
    • 34547761797 scopus 로고    scopus 로고
    • For amination of allylic alcohols, calculations revealed that dissociation of the olefin-ammonium is rate-determining step and is favored by strong π-acceptor ligands (that make the Pd electron-poor) since the more electron-rich is the metal, the more efficient is the back donation and consequently stronger is the Pd-olefin bond, see
  • 192
    • 34547736497 scopus 로고    scopus 로고
    • In this calculation the nucleophilic attack was also found thermodynamically favored by poor σ-donor ligands.
  • 194
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    • J.-C. Hierso, R. Smaliy, R. Amardeil, P. Meunier, Chem. Soc. Rev., in press.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.