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Volumn 30, Issue 3, 2011, Pages 611-617

Stille coupling of alkynyl stannane and aryl iodide, a many-pathways reaction: The importance of isomerization

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLS; ARYL IODIDES; C-C COUPLING; CATALYTIC PROCESS; CATALYTIC SYSTEM; KINETIC STUDY; OXIDATIVE ADDITIONS; STANNANE; STILLE COUPLING; STILLE REACTIONS; TRANSMETALATION;

EID: 79751501752     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100978w     Document Type: Article
Times cited : (34)

References (45)
  • 16
    • 79751488583 scopus 로고    scopus 로고
    • For "retrotransmetalation" we mean the exchange of an R on Pd for an X on Sn, the reverse of what happens in the so-called transmetalation.
    • For "retrotransmetalation" we mean the exchange of an R on Pd for an X on Sn, the reverse of what happens in the so-called transmetalation.
  • 21
    • 33847088632 scopus 로고
    • For cases of oxidative addition to neutral Pd(0) complexes by a concerted mechanism see
    • For cases of oxidative addition to neutral Pd(0) complexes by a concerted mechanism see: Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434-442
    • (1977) Acc. Chem. Res. , vol.10 , pp. 434-442
    • Stille, J.K.1    Lau, K.S.Y.2
  • 36
    • 79751491056 scopus 로고    scopus 로고
    • Strictly it is not a true equilibrium because of the continuous and irreversible formation of complex 7.
    • Strictly it is not a true equilibrium because of the continuous and irreversible formation of complex 7.
  • 37
    • 79751502225 scopus 로고    scopus 로고
    • For the concentration used in catalysis, about 90% of the coupling product is formed in 3 h. The reaction has an induction time, which suggests that probably the reaction is initiated only after some phosphine oxidation favoring dissociation has occurred. This ligand dissociation can be compensated in the presence of other external coordinating species that exist under catalytic conditions (e.g., alkynyl in large excess). Thus, under the conditions of Figures 1 and 2 the coupling is less than 5% in 3 h.
    • For the concentration used in catalysis, about 90% of the coupling product is formed in 3 h. The reaction has an induction time, which suggests that probably the reaction is initiated only after some phosphine oxidation favoring dissociation has occurred. This ligand dissociation can be compensated in the presence of other external coordinating species that exist under catalytic conditions (e.g., alkynyl in large excess). Thus, under the conditions of Figures 1 and 2 the coupling is less than 5% in 3 h.
  • 38
    • 79751492126 scopus 로고    scopus 로고
    • 3. See ref 21 for mechanistic details.
    • 3. See ref 21 for mechanistic details.
  • 39
    • 79751492997 scopus 로고    scopus 로고
    • The value obtained is slightly different from the reported data, which has been attributed to the eventual presence of traces of ligand in the slowest system or to the partial oxidation of phosphine in the fastest reaction. (21)
    • The value obtained is slightly different from the reported data, which has been attributed to the eventual presence of traces of ligand in the slowest system or to the partial oxidation of phosphine in the fastest reaction. (21)
  • 40
    • 79751481552 scopus 로고    scopus 로고
    • 5 for the same experiments. The values obtained are very similar (see the Supporting Information).
    • 5 for the same experiments. The values obtained are very similar (see the Supporting Information).
  • 41
    • 0027370376 scopus 로고
    • The multivariable adjustment program Gepasi was used:, See the Supporting Information for additional details.
    • The multivariable adjustment program Gepasi was used: Mendes, P. Comput. Appl. Biosci. 1993, 9, 563-571 See the Supporting Information for additional details.
    • (1993) Comput. Appl. Biosci. , vol.9 , pp. 563-571
    • Mendes, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.