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Volumn 352, Issue 18, 2010, Pages 3235-3240

Synthesis of dienes by palladium-catalyzed couplings of tosylhydrazones with aryl and alkenyl halides

Author keywords

cross coupling; dienes; ketones; palladium; tosylhydrazones

Indexed keywords


EID: 78650381983     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000700     Document Type: Article
Times cited : (76)

References (44)
  • 2
    • 20544450502 scopus 로고    scopus 로고
    • (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim
    • Metal-Catalyzed Cross-Coupling Reactions, (Eds.:, A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
  • 9
    • 78650378131 scopus 로고    scopus 로고
    • Metal-catalyzed C-H arylations
    • Metal-catalyzed C-H arylations
  • 13
    • 78650399978 scopus 로고    scopus 로고
    • Carbonyl α-arylations
    • Carbonyl α-arylations
  • 19
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    • references cited therein
    • Angew. Chem. Int. Ed. 2008, 47, 2127, and references cited therein.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 2127
  • 26
    • 78650350556 scopus 로고    scopus 로고
    • For related Pd-catalyzed processes based on diazo compounds, see
    • For related Pd-catalyzed processes based on diazo compounds, see
  • 37
    • 78650332293 scopus 로고    scopus 로고
    • The coupling reaction with hydrazones derived from less substituted acyclic α,β-unsaturated ketones, such as benzylideneacetone, gives rise, under optimized reaction conditions, to a 57: 43 mixture of the expected diene and the pyrazole that is formed by decomposition of the tosylhydrazone followed by electrocyclic ring closure
    • The coupling reaction with hydrazones derived from less substituted acyclic α,β-unsaturated ketones, such as benzylideneacetone, gives rise, under optimized reaction conditions, to a 57: 43 mixture of the expected diene and the pyrazole that is formed by decomposition of the tosylhydrazone followed by electrocyclic ring closure.
  • 38
    • 77956570131 scopus 로고    scopus 로고
    • The Pd-catalyzed synthesis of tetrasubstituted olefins by the reaction of tosylhydrazones with aryl halides has been recently published under slightly different reaction conditions:,. Nevertheless, we have observed that our protocol can be also employed for the preparation of simple tetrasubstituted alkenes
    • The Pd-catalyzed synthesis of tetrasubstituted olefins by the reaction of tosylhydrazones with aryl halides has been recently published under slightly different reaction conditions:, E. Brachet, A. Hamze, J.-F. Peyrat, J.-D. Brion, M. Alami, Org. Lett. 2010, 12, 4042. Nevertheless, we have observed that our protocol can be also employed for the preparation of simple tetrasubstituted alkenes.
    • (2010) Org. Lett. , vol.12 , pp. 4042
    • Brachet, E.1    Hamze, A.2    Peyrat, J.-F.3    Brion, J.-D.4    Alami, M.5
  • 39
    • 78650381568 scopus 로고    scopus 로고
    • -1 (ΔG) more stable than the TS of the β-hydride elimination from IV, that leads to the cross-conjugated diene. A very large energy difference may justify the exclusive formation of the linear dienes (see Supporting Information for details)
    • -1 (ΔG) more stable than the TS of the β-hydride elimination from IV, that leads to the cross-conjugated diene. A very large energy difference may justify the exclusive formation of the linear dienes (see Supporting Information for details).
  • 40
    • 78650407904 scopus 로고    scopus 로고
    • For some leading references regarding hydride eliminations on π-allylpalladium complexes see
    • For some leading references regarding hydride eliminations on π-allylpalladium complexes see
  • 44
    • 78650382640 scopus 로고    scopus 로고
    • The reaction with the hydrazone of 3-phenylpropanal led to a 10: 1 mixture of the dienes derived from β-hydride elimination and the vinylogous hydride elimination, respectively
    • The reaction with the hydrazone of 3-phenylpropanal led to a 10: 1 mixture of the dienes derived from β-hydride elimination and the vinylogous hydride elimination, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.