4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 37, Pages 9889-9892

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405183

Keywords

alkynes; annulation; benzamidines; CH activation; rhodium

Funding

  1. Ministry of Science and Technology of the Republic of China [NSC 102-2628-M-007-005]

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A new method for the synthesis of highly substituted naphthyridine-based polyheteroaromatic compounds in high yields proceeds through rhodium(III)-catalyzed multiple CH bond cleavage and CC and CN bond formation in a one-pot process. Such highly substituted polyheteroaromatic compounds have attracted much attention because of their unique -conjugation, which make them suitable materials for organic semiconductors and luminescent materials. Furthermore, a possible mechanism, which involves multiple chelation-assisted ortho CH activation, alkyne insertion, and reductive elimination, is proposed for this transformation.

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