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Volumn , Issue 16, 2011, Pages 2489-2498

Mechanistic insights into the palladium-catalysed asymmetric phosphination of cyclohexenyl triflate

Author keywords

C P coupling; Cross coupling; Homogeneous catalysis; Organophosphorus chemistry; Palladium; Phosphane ligands

Indexed keywords

CATALYSIS; CHEMICAL BONDS; ENANTIOSELECTIVITY; LIGANDS; PALLADIUM; REACTION INTERMEDIATES;

EID: 79956313779     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201000987     Document Type: Article
Times cited : (8)

References (34)
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    • For a recent review on the synthesis of alkenylphosphanes, see
    • For a recent review on the synthesis of alkenylphosphanes, see:, D. Julienne, O. Delacroix, A.-C. Gaumont, Curr. Org. Chem. 2010, 14, 457-482.
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    • Julienne, D.1    Delacroix, O.2    Gaumont, A.-C.3
  • 2
    • 77955116548 scopus 로고    scopus 로고
    • For a recent review on the application of alkenylphosphanes, see
    • For a recent review on the application of alkenylphosphanes, see:, D. Julienne, F. Toulgoat, O. Delacroix, A.-C. Gaumont, Curr. Org. Chem. 2010, 14, 1195-1222.
    • (2010) Curr. Org. Chem. , vol.14 , pp. 1195-1222
    • Julienne, D.1    Toulgoat, F.2    Delacroix, O.3    Gaumont, A.-C.4
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    • references cited therein
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    • Enantio-enriched (Sp)- 1 (98:2 e.r.) was prepared by (-)-sparteine- mediated asymmetric lithiation/trapping-reductive elimination as reported by:,. Only the (S) enantiomer is available by this method.
    • Enantio-enriched (Sp)- 1 (98:2 e.r.) was prepared by (-)-sparteine- mediated asymmetric lithiation/trapping-reductive elimination as reported by:, B. Wolfe, T. Livinghouse, J. Org. Chem. 2001, 66, 1514-1516. Only the (S) enantiomer is available by this method.
    • (2001) J. Org. Chem. , vol.66 , pp. 1514-1516
    • Wolfe, B.1    Livinghouse, T.2
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    • 0. It was prepared following chemistry developed by Brown et al. for the synthesis of arylic cationic oxidative complexes involved in the Heck reaction.
    • 0. It was prepared following chemistry developed by Brown et al. for the synthesis of arylic cationic oxidative complexes involved in the Heck reaction:, J. M. Brown, K. K. Hii, Angew. Chem. Int. Ed. Engl. 1996, 35, 657-659.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 657-659
    • Brown, J.M.1    Hii, K.K.2
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    • 85163237853 scopus 로고    scopus 로고
    • For the preparation of iodocyclohexene, see
    • For the preparation of iodocyclohexene, see
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    • 0027416248 scopus 로고
    • for characterization, see
    • K. Lee, D. F. Wiemer, Tetrahedron Lett. 1993, 34, 2433-2436 for characterization, see
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2433-2436
    • Lee, K.1    Wiemer, D.F.2
  • 21
    • 85163239065 scopus 로고    scopus 로고
    • note
    • Experimental details of the structure determination can be found in the Supporting Information. CCDC-CCDC-696197 contains the supplementary crystallographic data for compound 7. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
  • 22
    • 85163241022 scopus 로고    scopus 로고
    • note
    • THF was selected to ensure the complete deprotonation of the secondary phosphane-borane at low temperature, and DMF to stabilize the cationic complex 3.
  • 23
    • 85163236669 scopus 로고    scopus 로고
    • note
    • 4 leading to an incomplete reaction.
  • 25
    • 85163238388 scopus 로고    scopus 로고
    • note
    • 8]THF yielding phosphido-borane anion 4.
  • 27
    • 85163237023 scopus 로고    scopus 로고
    • note
    • This ratio depends on reaction conditions. We could not determine if this ratio of atropoisomers represents a kinetic or a thermodynamic preference or depends on other solution components.
  • 29
    • 85163238887 scopus 로고    scopus 로고
    • note
    • Experimental details of the structure determination can be found in the Supporting Information. CCDC-CCDC-696196 contains the supplementary crystallographic data for compound 5. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via.
  • 30
    • 85163238868 scopus 로고    scopus 로고
    • note
    • The apparent inversion is due to a Cahn-Ingold-Prelog priority change.
  • 32
    • 85163239713 scopus 로고    scopus 로고
    • For boron phosphide interconversion see, for example
    • For boron phosphide interconversion see, for example


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.