Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 20, Pages 6302-6308Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200188
Keywords
atom economy; cooperative effects; heterocycles; homogeneous catalysis; ruthenium
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Funding
- Fonds der Chemischen Industrie (FCI)
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Several ruthenium-catalyzed atom-economic transformations of propargyl alcohols with pyrroles or indoles leading to alkylated, propargylated, or annulated heteroaromatics are reported. The mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex containing a redox-coupled dienone ligand. The mode of activation regarding the propargyl alcohols determines the reaction pathway and depends on the alcohols substitution pattern. Secondary substrates form alkenyl complexes by a 1,2-hydrogen shift, whereas the transformation of tertiary substrates involves allenylidene intermediates. 1-Vinyl propargyl alcohols are converted by a cascade allylation/cyclization sequence. The environmentally benign processes are of broad scope and allow the selective synthesis of highly functionalized pyrroles and indoles generating water as the only waste product.
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