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Volumn 16, Issue 29, 2010, Pages 8596-8599

Palladium round trip in the Negishi coupling of trans- [PdMeCl(PMePh 2)2] with ZnMeCl: An experimental and DFT study of the transmetalation step

Author keywords

C C coupling; Density functional calculations; Homogeneous catalysis; Kinetics; Negishi coupling

Indexed keywords

C-C COUPLING; COUPLING PRODUCT; DENSITY-FUNCTIONAL CALCULATIONS; DFT STUDY; HOMOCOUPLING; HOMOGENEOUS CATALYSIS; NEGISHI COUPLING; NEGISHI REACTIONS; REDUCTIVE ELIMINATION; ROUND TRIP; TRANSMETALATION;

EID: 77955127651     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001332     Document Type: Article
Times cited : (69)

References (26)
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    • Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
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  • 13
    • 77955159438 scopus 로고    scopus 로고
    • 2] at 203 K. It is known that different oxidative addition mechanisms of alkyl halides are operational depending on the solvent and the halide, which affects the enantioselectivity of this step and the stereochemistry (cis or trans) of the kinetic product; however, in all experimental cases using alkyl halides in polar solvents the product observed is the trans isomer regardless of the enantioselectivity, showing that the cis-to-trans isomerization, if needed, is extremely fast, most likely faster than transmetalation
    • 2] at 203 K. It is known that different oxidative addition mechanisms of alkyl halides are operational depending on the solvent and the halide, which affects the enantioselectivity of this step and the stereochemistry (cis or trans) of the kinetic product; however, in all experimental cases using alkyl halides in polar solvents the product observed is the trans isomer regardless of the enantioselectivity, showing that the cis-to-trans isomerization, if needed, is extremely fast, most likely faster than transmetalation.
  • 17
    • 49449099994 scopus 로고    scopus 로고
    • For retro-transmetalation we mean the reverse of the transmetalation reaction. For a study of the retro-transmetalation in a Stille reaction see: M. H. Pérez-Temprano, A. Nova, J.A. Casares, P. Espinel, J. Am. Chem. Soc. 2008, 130, 10518-10519.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 10518-10519
    • Pérez-Temprano, M.H.1    Nova, A.2    Casares, J.A.3    Espinel, P.4
  • 18
    • 0027370376 scopus 로고
    • The multivariable adjust program Gepasi was used: a) P. Mendes, Comput. Appl. Biosci. 1993, 9, 563-571.
    • (1993) Comput. Appl. Biosci. , vol.9 , pp. 563-571
    • Mendes, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.