Catalytic C-H bond functionalization with palladium(II): Aerobic oxidative annulations of indoles

Journal of the American Chemical Society

Volumn 125, Issue 32, 2003, Pages 9578-9579

  Ferreira, Eric M ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; INDOLE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGEN BOND; OXIDATION; REACTION ANALYSIS; SUBSTITUTION REACTION;

CYCLIZATION; INDOLES; OXIDATION-REDUCTION; OXYGEN; PALLADIUM; PYRIDINES;

EID: 0041624424     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035054y     Document Type: Article

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16. a references.
17. a values to determine ligand nature may be an oversimplification, it has served as a useful gauge in our study.
18. Pd-black was observed in Table 1, entries 7-9.
19. 2 for these annulation reactions.
20. (b) Attempts to convert 1→2 using a variety of other Pd(II) oxidative protocols have met with minimum success, see Supporting Information.
21. (a) GC conversion was measured by consumption of 1 relative to an internal standard (tridecane).
22. (b) GC yield was measured by the amount of 2 relative to an internaI standard (tridecane).
23. 2. For a list of key references, see Supporting Information.
24. For control experiments, see Supporting Information.
25. 3 Thus. other possible effects cannot be ruled out, such as favorable interactions with catalytic intermediates. Studies elucidating the exact effect are underway.
26. Relative configuration determined by NOE analysis, see Supporting Information.