4.4 Article

InBr3 as a versatile and highly efficient catalyst for the synthesis of 3-allyl- and 3-benzylindoles

Journal

TETRAHEDRON LETTERS
Volume 48, Issue 35, Pages 6117-6120

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.06.144

Keywords

indium reagents; benzylic/allylic alcohols; indoles; benzylation; allylation

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Indoles undergo smooth alkylation with allylic and benzylic alcohols in the presence of 10 mol % of InBr3 under mild conditions to produce 3-allyl- and 3-benzyl indoles, respectively, in excellent yields and with high selectivity. This is the first example of the alkylation of indoles with benzylic alcohols using InBr3 as an acid catalyst. (c) 2007 Published by Elsevier Ltd.

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