期刊論文
| 學年 | 104 |
|---|---|
| 學期 | 2 |
| 出版（發表）日期 | 2016-03-17 |
| 作品名稱 | Synthesis and stability study of isocyano aryl boronate esters and their synthetic applications |
| 作品名稱（其他語言） | |
| 著者 | Hao-Ping Fang; Chia-Chieh Fu; Chin-Kuen Tai; Ken-Hao Chang; Ru-Han Yang; Meng-Ju Wu; Hsien-Chi Chen; Chia-Jung Li; Shi-Qing Huang; Wan-Hsiang Lien; Chih-Hsin Chen; Chung-Hung Hsieh; Bo-Cheng Wang; Siu-Fung Cheung; Po-Shen Pan |
| 單位 | |
| 出版者 | |
| 著錄名稱、卷期、頁數 | RSC Advances 6, pp.30362-30371 |
| 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. |
| 關鍵字 | boronate ester;isocyanide;multicomponent reaction |
| 語言 | en |
| ISSN | 2046-2069 |
| 期刊性質 | 國外 |
| 收錄於 | SCI |
| 產學合作 | |
| 通訊作者 | Po-Shen Pan (潘伯申) |
| 審稿制度 | 是 |
| 國別 | GBR |
| 公開徵稿 | |
| 出版型式 | ,電子版 |
| 相關連結 |
機構典藏連結 ( http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/107114 ) |