Synthesis and stability study of isocyano aryl boronate esters and their synthetic applications
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 )