Premium
Catalytic Prenylation and Reverse Prenylation of Indoles with Isoprene: Regioselectivity Manipulation through Choice of Metal Hydride
Author(s) -
Hu YanCheng,
Ji DingWei,
Zhao ChaoYang,
Zheng Hao,
Chen QingAn
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901025
Subject(s) - regioselectivity , prenylation , chemistry , catalysis , hydride , isoprene , selectivity , atom economy , combinatorial chemistry , organic chemistry , metal , polymer , copolymer , enzyme
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.