Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 16, Pages 5438-5442Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201901025
Keywords
indoles; isoprenes; metal hydrides; prenylation; reverse prenylation
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Funding
- Dalian Institute of Chemical Physics
- National Natural Science Foundation of China [21702204, 21801239]
- Chinese Academy of Sciences
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The basic industrial feedstock isoprene was employed as a building block to install prenyl and reverse-prenyl groups onto indoles. The regioselectivity can be manipulated by the choice of metal hydride. Reverse-prenylated indoles were attained with high selectivity when using Rh-H. By switching to a Pd-H catalyst, selectivity toward prenylated indoles was achieved. This regiodivergent method also features high atom economy without stoichiometric byproduct formation.
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