Ni-Catalyzed Cycloisomerization between 3-Phenoxy Acrylic Acid Derivatives and Alkynes via Intramolecular Cleavage and Formation of the C-O Bond To Give 2,3-Disubstituted Benzofurans
Ni-Catalyzed Cycloisomerization between 3-Phenoxy Acrylic Acid Derivatives and Alkynes via Intramolecular Cleavage and Formation of the C-O Bond To Give 2,3-Disubstituted Benzofurans
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DOI：
10.1021/acs.orglett.9b03170
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发表时间：
2019-10-18
期刊：
影响因子：
5.2
通讯作者：
Arisawa, Mitsuhiro
中科院分区：
文献类型：
--
作者：
Ohno, Shohei;Qiu, Jiawei;Arisawa, Mitsuhiro
基于过渡金属催化的C-O键断裂反应作为一种新的合成方法备受关注。到目前为止，已经报道了几种通过芳基醚、烯基醚、酯等的C-O键断裂发生的分子间反应。在这里，我们报道了 3-苯氧基丙烯酸衍生物前所未有的 C-O 键断裂，随后与炔烃形成分子内 C-O 键。该反应得到2,3-二取代苯并呋喃，其分别在2-位和3-位具有有用的官能团-甲硅烷基取代基和丙烯酸衍生物。该报告还描述了对该机制的理论（DFT）见解。
Reactions based on transition-metal-catalyzed C-O bond cleavage have attracted much attention as a new synthetic method. Until now, several intermolecular reactions via C-O bond cleavage of aryl ethers, alkenyl ethers, esters, and others have been reported. Here we report an unprecedented C-O bond cleavage of 3-phenoxy acrylic acid derivatives, followed by intramolecular C-O bond formation with alkynes. This reaction gave 2,3-disubstituted benzofurans having useful functional groups-silyl substituents and acrylic acid derivatives-at the 2- and 3-positions, respectively. This report also described theoretical (DFT) insights into the mechanism.