One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple CH Activation and Annulation

• Published in: Angewandte Chemie International Edition Vol. 53; no. 37; pp. 9889 - 9892
• Main Authors: Jayakumar, Jayachandran, Parthasarathy, Kanniyappan, Chen, Yi-Hsiang, Lee, Tai-Hua, Chuang, Shih-Ching, Cheng, Chien-Hong
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 08.09.2014; WILEY‐VCH Verlag; Wiley
• Subjects: Activation; Alkynes; annulation; benzamidines; Bonding; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Cleavage; CH activation; Insertion; Organic chemistry; Physical Sciences; rhodium; Science & Technology; Synthesis; Transformations; DIRECTING GROUP; O BOND; alkynes; INTERNAL ALKYNES; ISOQUINOLONE SYNTHESIS; annulation; CH activation; COUPLING REACTIONS; benzamidines; N BOND FORMATION; ARYL KETONES; CATALYZED OXIDATIVE COUPLING/CYCLIZATION; rhodium; RHODIUM CATALYSIS; BENZOIC-ACIDS; CH activation
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201405183

A new method for the synthesis of highly substituted naphthyridine‐based polyheteroaromatic compounds in high yields proceeds through rhodium(III)‐catalyzed multiple CH bond cleavage and CC and CN bond formation in a one‐pot process. Such highly substituted polyheteroaromatic compounds have attracted much attention because of their unique π‐conjugation, which make them suitable materials for organic semiconductors and luminescent materials. Furthermore, a possible mechanism, which involves multiple chelation‐assisted ortho CH activation, alkyne insertion, and reductive elimination, is proposed for this transformation. Activated and annulated: A rhodium‐catalyzed one‐pot synthesis of highly substituted polyheteroaromatic compounds from N‐hydroxybenzamidines and alkynes is described. This reaction likely proceeds through multiple CH bond activation and annulation.