Journal
TETRAHEDRON
Volume 65, Issue 16, Pages 3120-3129Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.043
Keywords
Cross-coupling; Indoles; Silanols; Palladium catalysis; Alkynes
Categories
Funding
- NIGMS NIH HHS [R01 GM063167-08, R01 GM063167] Funding Source: Medline
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A simple and convergent synthesis of 2,3-disubstituted indoles has been developed using a sequential Larock indole synthesis and silicon-based, cross-coupling reaction. Substituted 2-iodoanilines reacted with an alkynyldimethylsilyl tert-butyl ether to afford indole-2-silanols under the Larock hetero-annulation conditions after hydrolysis. The corresponding sodium 2-indolylsilanolate salts successfully engaged in cross-coupling with aryl bromides and chlorides to afford multi-substituted indoles. The development of an alkynyldimethylsilyl tert-butyl ether as a masked silanol equivalent enabled a smooth heteroannulation process and the identification of a suitable catalyst/ligand combination provided for a facile cross-coupling reaction. (C) 2008 Elsevier Ltd. All rights reserved.
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