Sequential SNAr Reaction/Suzuki-Miyaura Coupling/C−H Direct Arylations Approach for the Rapid Synthesis of Tetraaryl-Substituted Pyrazoles
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...
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| Published in | Chemistry, an Asian journal Vol. 10; no. 8; pp. 1626 - 1630 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
Blackwell Publishing Ltd
01.08.2015
Wiley Subscription Services, Inc |
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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.
Cote dpyrazole: A rapid synthesis of 1,3,4,5‐tetraaryl‐substituted pyrazoles has been achieved through a sequence based on a readily available 3‐iodo‐1H‐pyrazole scaffold; this sequence includes a SNAr reaction, Suzuki–Miyaura coupling, and C−H direct arylations. This is the first example of the synthesis of pyrazoles with four different aryl groups by four sequential cross‐coupling reactions. |
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| AbstractList | 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.
Cote dpyrazole: A rapid synthesis of 1,3,4,5‐tetraaryl‐substituted pyrazoles has been achieved through a sequence based on a readily available 3‐iodo‐1H‐pyrazole scaffold; this sequence includes a SNAr reaction, Suzuki–Miyaura coupling, and C−H direct arylations. This is the first example of the synthesis of pyrazoles with four different aryl groups by four sequential cross‐coupling reactions. 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. |
| Author | Johmoto, Kohei Uekusa, Hidehiro Matsumura, Keisuke Takahashi, Takashi Morita, Taiki Fuse, Shinichiro Kobayashi, Daisuke |
| Author_xml | – sequence: 1 givenname: Taiki surname: Morita fullname: Morita, Taiki organization: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, 152-8552, Tokyo, Japan – sequence: 2 givenname: Daisuke surname: Kobayashi fullname: Kobayashi, Daisuke organization: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, 152-8552, Tokyo, Japan – sequence: 3 givenname: Keisuke surname: Matsumura fullname: Matsumura, Keisuke organization: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, 152-8552, Tokyo, Japan – sequence: 4 givenname: Kohei surname: Johmoto fullname: Johmoto, Kohei organization: Department of Chemistry and Materials Science, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, 152-8551, Tokyo, Japan – sequence: 5 givenname: Hidehiro surname: Uekusa fullname: Uekusa, Hidehiro organization: Department of Chemistry and Materials Science, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, 152-8551, Tokyo, Japan – sequence: 6 givenname: Shinichiro surname: Fuse fullname: Fuse, Shinichiro email: sfuse@res.titech.ac.jp organization: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, 152-8552, Tokyo, Japan – sequence: 7 givenname: Takashi surname: Takahashi fullname: Takahashi, Takashi organization: Yokohama College of Pharmacy, 601, Matano-cho, Totsuka-ku, Yokohama, 245-0066, Kanagawa, Japan |
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| Snippet | 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... 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... |
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| SubjectTerms | C-H activation Chemistry cross-coupling heterocycles palladium synthetic methods |
| Title | Sequential SNAr Reaction/Suzuki-Miyaura Coupling/C−H Direct Arylations Approach for the Rapid Synthesis of Tetraaryl-Substituted Pyrazoles |
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