Hattori Tomohiro, Ueda Shun, Takakura Ryoya, Sawama Yoshinari, Monguchi Yasunari, Sajiki Hironao
Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, 501-1196, Japan.
Chemistry. 2017 Jun 16;23(34):8196-8202. doi: 10.1002/chem.201606048. Epub 2017 Apr 10.
Carbon monoxide (CO) and styrene derivatives that can be both generated by a palladium on carbon (Pd/C)-catalyzed carbon-carbon (C-C) bond cleavage reaction of cinnamaldehyde derivatives were effectively utilized in further palladium-catalyzed C-C bond forming reactions in a direct and practical way. CO derived from simple and affordable CO carriers such as cinnamaldehyde or terephthalaldehyde was efficiently employed in the in situ CO fixation with various aromatic iodides through a palladium-catalyzed carbonylation followed by an inter- or intramolecular coupling reaction with alcohols to afford the corresponding esters or lactones, respectively. Styrene derivatives were also efficient substrates in an in situ Mizoroki-Heck-type cross-coupling reaction with aryl iodides, leading to the effective formation of asymmetric stilbenes. The decarbonylation of cinnamaldehyde derivatives and the subsequent independent syntheses of both esters/lactones and 1,2-diarylethenes could be achieved in a virtual one-pot and in situ reaction using a H-shaped pressure-tight glass-sealed tube consisting of two independent but laterally connected reaction tubes in the gas space.
一氧化碳（CO）和苯乙烯衍生物可通过钯碳（Pd/C）催化肉桂醛衍生物的碳-碳（C-C）键裂解反应生成，它们以直接且实用的方式有效地用于进一步的钯催化C-C键形成反应。源自简单且价格低廉的CO载体（如肉桂醛或对苯二甲醛）的CO通过钯催化的羰基化反应，与各种芳基碘化物进行原位CO固定，随后分别与醇进行分子间或分子内偶联反应，以分别得到相应的酯或内酯。苯乙烯衍生物也是与芳基碘化物进行原位Mizoroki-Heck型交叉偶联反应的有效底物，从而有效地形成不对称芪。使用由两个独立但在气体空间中横向连接的反应管组成的H形耐压玻璃密封管，可以在虚拟的一锅法原位反应中实现肉桂醛衍生物的脱羰反应以及随后酯/内酯和1,2-二芳基乙烯的独立合成。
