Potassium iodide catalyzed simultaneous C3-formylation and N-aminomethylation of indoles with 4-substituted-N,N-dimethylanilines.

Potassium iodide catalyzed simultaneous C3-formylation and N-aminomethylation of indoles with 4-substituted-N,N-dimethylanilines.

Organic & biomolecular chemistry (2012-11-13)

Lan-Tao Li, Hong-Ying Li, Li-Juan Xing, Li-Juan Wen, Peng Wang, Bin Wang

ABSTRACT

A one-pot dual functionalization of indoles has been developed. The simultaneous C3-formylation and N-aminomethylation of indoles can be achieved using readily available potassium iodide as a catalyst and tert-butyl peroxybenzoate as a co-oxidant.

MATERIALS

Product Number

Brand

Product Description

P8166

Sigma-Aldrich

Potassium iodide, suitable for plant cell culture

P2963

Sigma-Aldrich

Potassium iodide, BioXtra, ≥99.0%

49636

Supelco

N-Methylaniline, analytical standard

65760

Sigma-Aldrich

N-Methylaniline, purum, ≥98.0% (GC)

60399

Sigma-Aldrich

Potassium iodide, BioUltra, ≥99.5% (AT)

60422

Sigma-Aldrich

Potassium iodide, tested according to Ph. Eur.

77505

Sigma-Aldrich

Potassium iodide, purum p.a., ≥99.0% (AT)

204102

Sigma-Aldrich

Potassium iodide, ≥99.99% trace metals basis

429422

Sigma-Aldrich

Potassium iodide, AnhydroBeads^™, −10 mesh, 99.998% trace metals basis

209872

Sigma-Aldrich

4-tert-Butyl-N,N-dimethylaniline, 98%

M29304

Sigma-Aldrich

N-Methylaniline, 98%

24-4860

Sigma-Aldrich

Potassium iodide, JIS special grade, ≥99.5%

24-4870

Sigma-Aldrich

Potassium iodide, SAJ first grade, ≥99.5%

24-4825

Sigma-Aldrich

Potassium iodide solution, 15 % (w/v)

236233

Sigma-Aldrich

N-Methylaniline, ≥99%

221945

Sigma-Aldrich

Potassium iodide, ACS reagent, ≥99.0%

03124

Sigma-Aldrich

Potassium iodide, puriss., meets analytical specification of Ph. Eur. BP, USP, 99.0-100.5% (calc. to the dried substance)

207969

Sigma-Aldrich

Potassium iodide, ReagentPlus^®, 99%

651818

Sigma-Aldrich

Gold etchant, standard