Catalytic Prenylation and Reverse Prenylation of Indoles with Isoprene: Regioselectivity Manipulation through Choice of Metal Hydride. (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. Volume 131:Number 16(2019)
• Page Start: 5492
• Page End: 5496
• Publication Date: 2019-03-12
• Subjects: Indole -- Isoprene -- Metallhydride -- Prenylierung -- Reverse Prenylierung; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201901025
• Languages: English
• ISSNs: 0044-8249

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.