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Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids
| Title: | Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids |
| Authors: | Vishal Kumar, Rawat Browse this author | | Kosuke, Higashida Browse this author | | Masaya, Sawamura Browse this author →KAKEN DB |
| Keywords: | Silver catalyst | | Cooperative catalysis | | N-Heterocyclic carbene | | Cyclization |
| Issue Date: | 16-Mar-2021 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | Advanced Synthesis & Catalysis |
| Volume: | 363 |
| Issue: | 6 |
| Start Page: | 1631 |
| End Page: | 1637 |
| Publisher DOI: | 10.1002/adsc.202001515 |
| Abstract: | Silver complexes with 5-(4-(tert-butyl)-1H-imidazol-1-yl)-imidazo[1,5-a]pyridin-3-ylidene ligands were synthesized as metal-imidazole acid-base cooperative catalysts. Single crystal XRD analysis revealed that the silver atom was located in the vicinity of the imidazole ring and that cationic silver complexes formed dimers through coordination between the silver metal and the imidazole pendant. These cationic silver complexes served as catalysts for cyclization of alkyne-tethered carboxylic acids. NMR experiments indicated that the dimeric cationic silver complex dissociated to a monomer upon protonation of the imidazole moiety, resulting in coordination of an acetonitrile to the silver atom. DFT calculations supported the acid-base cooperative action of the silver-imidazole for the efficient alkyne-carboxylic acid cyclization. |
| Rights: | This is the peer reviewed version of the following article: Advanced synthesis & catalysis Volume363, Issue6 March 16, 2021 Pages 1631-1637, which has been published in final form at https://onlinelibrary.wiley.com/doi/10.1002/adsc.202001515. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/84394 |
| Appears in Collections: | 理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 澤村 正也
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