Sequential SNAr Reaction/Suzuki–Miyaura Coupling/C−H Direct Arylations Approach for the Rapid Synthesis of Tetraaryl‐Substituted Pyrazoles |
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| Authors: | Taiki Morita Daisuke Kobayashi Keisuke Matsumura Dr Kohei Johmoto Dr Hidehiro Uekusa Dr Shinichiro Fuse Prof Dr Takashi Takahashi |
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| Institution: | 1. Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Tokyo, Japan;2. Department of Chemistry and Materials Science, Tokyo Institute of Technology, 2-12-1, Tokyo, Japan;3. Chemical Resources Laboratory, Tokyo Institute of Technology, 4259, Yokohama, Japan;4. Yokohama College of Pharmacy, 601, Kanagawa, Japan |
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| Abstract: | A rapid synthesis of 1,3,4,5‐tetraaryl‐substituted pyrazoles has been achieved through a sequence of SNAr reaction/Suzuki–Miyaura coupling/Pd‐catalyzed direct arylations that used 3‐iodo‐1H‐pyrazole as a scaffold. Pyrazoles with four different aryl groups were synthesized in a straightforward manner with no extra synthetic steps, such as protection/deprotection or the introduction of activating/directing groups, using readily available substrates and reagents. The developed synthetic approach enabled the structurally diverse synthesis of multiaryl‐substituted pyrazoles without using a glovebox technique. |
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| Keywords: | C-H activation cross-coupling heterocycles palladium synthetic methods |
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