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- Title
Catalytic Prenylation and Reverse Prenylation of Indoles with Isoprene: Regioselectivity Manipulation through Choice of Metal Hydride.
- Authors
Hu, Yan‐Cheng; Ji, Ding‐Wei; Zhao, Chao‐Yang; Zheng, Hao; Chen, Qing‐An
- Abstract
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.
- Subjects
PALLADIUM catalysts; ISOPRENYLATION; ISOPRENE; REGIOSELECTIVITY (Chemistry); HYDRIDES; STOICHIOMETRY
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 16, p5492
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201901025