教師資料查詢 | 類別: 期刊論文 | 教師: 王伯昌 WANG, BO-CHENG (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
語言英文
ISSN2046-2069
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
國別英國
公開徵稿
出版型式,電子版
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