Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 17, Pages 6442-6451Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901224k
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Funding
- National Institutes of Health [R01GM084945]
- Petroleum Research Fund [46850-G1]
- University of Illinois at Chicago
- Division of Research Resources
- National Institutes of Health
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The use of a rhodium(II) carboxylate catalyst enables the mild and stereoselective formation of carbazoles from biaryl azides. Intramolecular competition experiments of triaryl azides suggested the source of the selectivity. A primary intramolecular kinetic isotope effect was not observed, and correlation of the product ratios with Hammett sigma(+) values produced a plot with two intersecting lines with opposite rho values. These data suggest that electronic donation by the biaryl pi-system accelerates the formation of rhodium nitrenoid and that C-N bond formation occurs through a 4 pi-electron-5-atom electrocyclization.
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