Fast and Highly Regioselective Allylation of Indole and Pyrrole Compounds by Allyl Alcohols Using Ru-Sulfonate Catalysts

New Ru-sulfonate catalysts have been synthesized and shown to very rapidly allylate indole and pyrrole compounds using allyl alcohols as substrates. The observed regioselectivity is exceptionally high (up to 100% of the branched isomer). Density functional theory calculations explain these results.

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-09, Vol.130 (35), p.11604-11605
Main Authors: Zaitsev, Alexey B, Gruber, Stefan, Plüss, Pascal A, Pregosin, Paul. S, Veiros, Luis F, Wörle, Michael
Format: Article
Language:English
Subjects:
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Catalysis
Indoles - chemical synthesis
Indoles - chemistry
Models, Molecular
Propanols - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Ruthenium Compounds - chemical synthesis
Ruthenium Compounds - chemistry
Sulfonic Acids - chemical synthesis
Sulfonic Acids - chemistry
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Description
Summary:New Ru-sulfonate catalysts have been synthesized and shown to very rapidly allylate indole and pyrrole compounds using allyl alcohols as substrates. The observed regioselectivity is exceptionally high (up to 100% of the branched isomer). Density functional theory calculations explain these results.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja804379k