Preparation of Fluorescent Materials from Biomass-Derived Furfural and Natural Amino Acid Cysteine through Cross-Coupling Reactions for Extended π-Conjugation
Preparation of Fluorescent Materials from Biomass-Derived Furfural and Natural Amino Acid Cysteine through Cross-Coupling Reactions for Extended π-Conjugation
复制标题
通过交叉偶联反应扩展π-共轭从生物质衍生的糠醛和天然氨基酸半胱氨酸制备荧光材料
DOI：
10.1055/s-0034-1380460
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发表时间：
2015
期刊：
影响因子：
2
通讯作者：
Atsunori Mori
中科院分区：
文献类型：
--
作者：
Shota Tanaka;Kana Ashida;Go Tatsuta;Atsunori Mori
以生物质衍生的杂环化合物糠醛和天然氨基酸半胱氨酸为原料，经四步反应制得2-呋喃并-4-甲酸甲酯。一锅溴化，然后在钯催化下与芳基硼酸盐在呋喃环上芳基化得到芳基化的呋喃并噻唑，产率很高。在AGF的存在下，噻唑环(5位)上的C-H键进一步芳基化得到了具有强烈光致发光性能的二芳基呋喃并噻唑类化合物。在噻唑的C-H键上还与AGF进行了同位偶联反应，得到了相应的由八个(杂环)芳环组成的进一步共轭产物。
Preparation of 2-furylthiazole-4-carboxylic acid methyl ester is achieved in four steps from biomass-derived heteroaromatic compound furfural and a natural amino acidl-cysteine. One-pot bromination and following palladium-catalyzed arylation with arylboronates of the thus obtained furylthiazole at the furan ring gives arylated furylthiazole in excellent yields. Further arylation at the C–H bond of the thiazole ring (5-position) in the presence of AgF as an additive leads to diarylated furylthiazoles, which show strong photoluminescence. Homocoupling at the C–H bond of thiazole is also carried out with AgF to afford the corresponding further conjugated product composed of eight (hetero)aromatic rings.