The Copper-Catalyzed C-3-Formylation of Indole CH Bonds using Tertiary Amines and Molecular Oxygen

• Published in: Advanced synthesis & catalysis Vol. 354; no. 13; pp. 2438 - 2442
• Main Authors: Chen, Jianbin, Liu, Bin, Liu, Dongfang, Liu, Shan, Cheng, Jiang
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 17.09.2012; WILEY‐VCH Verlag; Wiley; Wiley-VCH; Wiley Subscription Services, Inc
• Subjects: aldehydes; Amines; Carbonyls; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Cleaning; Copper; CH activation; Exact sciences and technology; formylation; Functional groups; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Indoles; Organic chemistry; Oxidizing agents; Oxygen; Physical Sciences; Preparations and properties; Science & Technology; Synthesis; tertiary amines; Tolerances; tertiary amines; ACTIVATION; DIRECT ARYLATION; TETRAHYDROISOQUINOLINES; formylation; TERMINAL ALKYNES; C?H activation; DEHYDROGENATIVE COUPLING CDC; DIRECT ALKYNYLATION; OXIDATIVE CYANATION; aldehydes; copper; AEROBIC OXIDATION; SINGLET OXYGEN; HYDROGEN-PEROXIDE; Water; Catalytic reaction; Carbon-hydrogen bond; Nitrogen heterocycle; Chemical bond; N,N,N',N'-tetramethylethylenediamine; Transition metal; Oxidant; Aldehyde; Ketone; Oxygen molecules; C―H activation; Copper ion; Tertiary amine; Formylation; Copper; Indole derivatives; Functional group
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201200345

A copper‐catalyzed formylation reaction has been developed by employing oxygen (O2) as the clean oxidant. The CH bonds of indoles were C‐3‐formylated by tetramethylethylenediamine (TMEDA) and water (H2O; in situ formed and external added water) as the carbonyl source in moderate to good yields with good functional group tolerance. Thus, it represents a facile procedure leading to 3‐formylindoles.