Catalytic Prenylation and Reverse Prenylation of Indoles with Isoprene: Regioselectivity Manipulation through Choice of Metal Hydride.
indoles
isoprenes
metal hydrides
prenylation
reverse prenylation
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 04 2019
08 04 2019
Historique:
received:
25
01
2019
revised:
07
02
2019
pubmed:
13
2
2019
medline:
13
2
2019
entrez:
13
2
2019
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 30748079
doi: 10.1002/anie.201901025
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
5438-5442Subventions
Organisme : National Natural Science Foundation of China
ID : 21702204
Pays : International
Organisme : National Natural Science Foundation of China
ID : 21801239
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.