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An Improved Procedure for Aryne Generation from o-Triazenylarylboronic Acids through One-Pot Boronate Formation/Silica Gel Treatment |
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| Authors: | Dr. Motoki Ito Haruna Yamazaki Aguri Ito Ryuhei Oda Moeka Komiya Dr. Kazuhiro Higuchi Prof. Dr. Shigeo Sugiyama |
| Affiliation: | 1. Meiji Pharmaceutical University, 2-522-1 Noshio Kiyose, Tokyo, 204-8588 Japan;2. Meiji Pharmaceutical University, 2-522-1 Noshio Kiyose, Tokyo, 204-8588 Japan Contribution: Data curation (supporting), Investigation (lead);3. Meiji Pharmaceutical University, 2-522-1 Noshio Kiyose, Tokyo, 204-8588 Japan Contribution: Investigation (supporting);4. Meiji Pharmaceutical University, 2-522-1 Noshio Kiyose, Tokyo, 204-8588 Japan Contribution: Data curation (supporting), Formal analysis (supporting), Investigation (supporting) |
| Abstract: | We have developed an improved method for generating aryne from o-triazenylarylboronic acids. Unlike the previous method that required excess o-triazenylarylboronic acids as aryne precursors, we used corresponding boronates as limiting reagents, which resulted in high yields. By combining the formation of boronates and aryne generation through silica gel treatment in one-pot, we were able to effectively use a wide range of o-triazenylarylboronic acids in reactions with various arynophiles. This one-pot method was particularly suitable for transforming complex aryne precursors with different functional groups. |
| Keywords: | aryne boronic acid one-pot reaction synthetic methods triazene |