教師資料查詢 | 類別: 期刊論文 | 教師: 謝忠宏 HSIEH, CHUNG-HUNG (瀏覽個人網頁)

標題: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;
單位
出版者
著錄名稱、卷期、頁數RSC Advances 6(36), p.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
語言英文(美國)
ISSN
期刊性質國外
收錄於SCI;
產學合作
通訊作者
審稿制度
國別中華民國
公開徵稿
出版型式,電子版,紙本
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