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- Title
Metal‐Free Oxidative Cross Coupling of Indoles with Electron‐Rich (Hetero)arenes.
- Authors
Caramenti, Paola; Nandi, Raj Kumar; Waser, Jerome
- Abstract
Abstract: A new method for the synthesis of bi‐heteroaryls is reported, based on the umpolung of indoles with benziodoxol(on)e hypervalent iodine reagents (IndoleBX). The oxidative coupling of IndoleBX with an equimolar amount of electron‐rich benzenes, indoles, pyrroles, and thiophenes proceeded under mild transition‐metal‐free conditions. Functionalized non‐symmetrical bi‐indolyl heterocycles were accessed efficiently. Introduction of a new type of C2‐substituted indole benziodoxole reagents further allowed extending the scope of the reaction to NH unprotected and C3‐alkylated indoles. The obtained bi‐heterocycles are important building blocks in synthetic and medicinal chemistry, and could be easily transformed into more complex heterocyclic systems.
- Subjects
INDOLE compounds; COUPLING reactions (Chemistry); AROMATIC compound synthesis; THIOPHENES; PYRROLES
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 40, p10049
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201802142