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    Title: Synthesis and stability study of isocyano aryl boronate esters and their synthetic applications
    Authors: 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
    Keywords: boronate ester;isocyanide;multicomponent reaction
    Date: 2016-03-17
    Issue Date: 2016-08-15
    Publisher: Royal Society of Chemistry
    Abstract: 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.
    Relation: RSC Advances 6, pp.30362-30371
    DOI: 10.1039/c5ra27624a
    Appears in Collections:[化學學系暨研究所] 期刊論文

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