Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 33, Pages 11416-11417Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1052335
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- University of Toronto
- Merck-Frosst Canada for an industrial research chair
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A Pd(0)-catalyzed C-N bond-forming reaction leading to the synthesis of brominated indoles is described. The use of the phosphine ligand PtBu3 is necessary for reactivity. It is proposed that the bulky ligand serves to prevent inhibition of the catalyst by facilitating reversible oxidative addition into the product C-Br bond. Intramolecular coupling of a vinyl bromide in the presence of an aryl iodide can take place, demonstrating unprecedented levels of selectivity.
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