Substituent Effect of Imino-O-arenesulfonates, a Coupling Partner in Suzuki-Miyaura Reaction for Substitution of the Pyrazine Ring: A Study for the Synthesis of Coelenterazine Analogs
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- Makarasen Arthit
- Graduate School of Bioagricultural Sciences, Nagoya University
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- Kuse Masaki
- Institute of Material Science, Nagoya University
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- Nishikawa Toshio
- Graduate School of Bioagricultural Sciences, Nagoya University
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- Isobe Minoru
- Graduate School of Bioagricultural Sciences, Nagoya University Institute for Advanced Research, Nagoya University
Bibliographic Information
- Other Title
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- Substituent Effect of Imino-<i>O</i>-arenesulfonates, a Coupling Partner in Suzuki–Miyaura Reaction for Substitution of the Pyrazine Ring: A Study for the Synthesis of Coelenterazine Analogs
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Abstract
Amino(aryl)pyrazines, a key intermediate in the synthesis of coelenterazine and its analogs, can be prepared in excellent yields by utilizing imino-O-tosylates in the Suzuki–Miyaura reaction. These imino-O-tosylates serve as a substitute for the corresponding imino-O-triflates, which are sometimes too unstable to be stored during the optimization of the reaction conditions. Aryltrifluoroborates, a coupling partner, worked well when arylboronic acids or arylboronate esters were less reactive. Aryltrifluoroborates also worked well when containing an electron-donating group attached to the aromatic ring. The study of the substituent effect of imino-O-arenesulfonates demonstrated a major difference in the rate of the reactions when changing from electron-donating groups to electron-withdrawing groups at the para position of arenesulfonates. Imino-O-arenesulfonate containing a para-bromo substituent only gave the desired coupling product leaving the para substituent of arenesulfonate untouched.
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 82 (7), 870-878, 2009
The Chemical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679118352000
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- NII Article ID
- 130004152630
- 10025126416
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- NII Book ID
- AA00580132
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- ISSN
- 13480634
- 00092673
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- NDL BIB ID
- 10277050
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed