Skip to Content
Merck
  • FeCl3-mediated Friedel-Crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines.

FeCl3-mediated Friedel-Crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines.

Angewandte Chemie (International ed. in English) (2012-11-06)
Rodolphe Beaud, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent
PMID23125000
ABSTRACT

IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl(3) features a rare example of the electrophilic reactivity of the indole core in a Friedel-Crafts reaction. This indole umpolung allows us straightforward access to the tetracyclic benzofuroindoline motif found in the natural product diazonamide A, which is a potent antitumor agent.

MATERIALS
Product Number
Brand
Product Description
F2877
Sigma-Aldrich
Iron(III) chloride hexahydrate, reagent grade, ≥98%, chunks
44944
Sigma-Aldrich
Iron(III) chloride hexahydrate, puriss. p.a., ACS reagent, crystallized, 98.0-102% (RT)
701122
Sigma-Aldrich
Iron(III) chloride, sublimed grade, ≥99.9% trace metals basis
451649
Sigma-Aldrich
Iron(III) chloride, anhydrous, powder, ≥99.99% trace metals basis
W259306
Sigma-Aldrich
Indole, ≥99%, FG
I3408
Sigma-Aldrich
Indole, ≥99%
236489
Sigma-Aldrich
Iron(III) chloride hexahydrate, ACS reagent, 97%
710857
Sigma-Aldrich
Iron(III) chloride solution, 0.2 M in 2-methyltetrahydrofuran
80353
Millipore
TDA Reagent, suitable for microbiology
I5605
Sigma-Aldrich
Indoline, ReagentPlus®, 99%
12322
Sigma-Aldrich
Iron(III) chloride solution, purum, 45% FeCl3 basis