One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple CH Activation and Annulation†
Jayachandran Jayakumar
Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorDr. Kanniyappan Parthasarathy
Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorYi-Hsiang Chen
Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorTai-Hua Lee
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30013 (Taiwan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Shih-Ching Chuang
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30013 (Taiwan)
Shih-Ching Chuang, Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30013 (Taiwan)
Chien-Hong Cheng, Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorCorresponding Author
Prof. Dr. Chien-Hong Cheng
Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Shih-Ching Chuang, Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30013 (Taiwan)
Chien-Hong Cheng, Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorJayachandran Jayakumar
Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorDr. Kanniyappan Parthasarathy
Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorYi-Hsiang Chen
Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorTai-Hua Lee
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30013 (Taiwan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Shih-Ching Chuang
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30013 (Taiwan)
Shih-Ching Chuang, Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30013 (Taiwan)
Chien-Hong Cheng, Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorCorresponding Author
Prof. Dr. Chien-Hong Cheng
Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Shih-Ching Chuang, Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30013 (Taiwan)
Chien-Hong Cheng, Department of Chemistry, National Tsing Hua University, Hsinchu 30013 (Taiwan) http://mx.nthu.edu.tw/%7Echcheng
Search for more papers by this authorWe thank the Ministry of Science and Technology of the Republic of China (NSC 102-2628-M-007-005) for support of this research.
Graphical Abstract
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 CH bond activation and annulation.
Abstract
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 π-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.
Supporting Information
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