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| 題名: | Synthesis and stability study of isocyano aryl boronate esters and their synthetic applications |
| 作者: | Fang, Hao-Ping;Fu, Chia-Chieh;Tai, Chin-Kuen;Chang, Ken-Hao;Yang, Ru-Han;Wu, Meng-Ju;Chen, Hsien-Chi;Li, Chia-Jung;Huang, Shi-Qing;Lien, Wan-Hsiang |
| 日期: | 2016-03-17 |
| 上傳時間: | 2018-03-15 12:10:57 (UTC+8) |
| 摘要: | A facile synthesis of isocyano arylboronate esters is reported. Although tri-coordinate boron functional groups are commonly recognized as vulnerable to nucleophilic attack, the newly reported tri-coordinate isocyano arylboronate esters were found to be stable, albeit owing to the presence of an isocyano group. Theoretical calculations, using the DFT/B3LYP/6-31G(d,p) method, revealed that the electron delocalization between the aryl group and the boron atom might contribute to this stability. UV-vis spectroscopic investigations on 2-(4-isocyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2a) were in agreement with the theoretical studies, showing a red-shifted absorption compared with that of phenylisonitrile. The reported strategy allows boronate ester substrates to survive throughout two-step operations. Two of the compounds synthesized were successfully exploited in Ugi and Passerini multicomponent reactions to afford corresponding products. In addition, two boron-containing tetrazoles were also prepared under environmentally benign conditions. These results demonstrated that functionalized isocyanides are stable and can be used as strategically as synthetic building blocks. |
| 關聯: | RSC Advances 6(36), p.30362-30371 |
| DOI: | 10.1039/C5RA27624A |
| 顯示於類別: | [化學學系暨研究所] 期刊論文
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