Catalytic Prenylation and Reverse Prenylation of Indoles with Isoprene: Regioselectivity Manipulation through Choice of Metal Hydride. Issue 16 (12th March 2019)

• Record Type: Journal Article
• Authors: Hu, Yan‐Cheng; Ji, Ding‐Wei; Zhao, Chao‐Yang; Zheng, Hao; Chen, Qing‐An
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 16(2019)
• Page Start: 5438
• Page End: 5442
• Publication Date: 2019-03-12
• Subjects: indoles -- isoprenes -- metal hydrides -- prenylation -- reverse prenylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201901025
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Backwards and forwards : A metal hydride mediated regiodivergent coupling of indoles with the industrial feedstock isoprene was developed for which the regioselectivity for prenylation versus reverse prenylation is determined by the choice of metal hydride. This method enables the installation of prenyl and reverse‐prenyl motifs onto indoles with high atom economy.