Boronic Acid‐Mediated Photocatalysis Enables the Intramolecular Hydroacylation of Olefins Using Carboxylic Acids

Boronic Acid‐Mediated Photocatalysis Enables the Intramolecular Hydroacylation of Olefins Using Carboxylic Acids
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DOI:
10.1002/ejoc.202200082
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发表时间:
2022-03
影响因子:
2.8
通讯作者:
Taichi Yumura;Takeshi Nanjo;Y. Takemoto
Taichi Yumura;Takeshi Nanjo;Y. Takemoto
中科院分区:
化学3区
文献类型:
--
作者:
Taichi Yumura;Takeshi Nanjo;Y. Takemoto

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发展了一种用羧酸(CA)进行的烯烃分子内氢酰化反应。在硼酸的辅助下,CaS可作为可见光催化光氧化还原反应中的酰基自由基前驱体。CA很容易转化为相应的环酮,而不需要使用任何化学计量比的活化剂。机理研究表明,CA和硼酸形成的“ATE”络合物对于从未反应的羧基生成相当于酰基的自由基是至关重要的。
An intramolecular hydroacylation of olefins using carboxylic acids (CAs) has been developed. With the aid of a boronic acid, CAs can be used as acyl‐radical precursors in catalytic photoredox reactions driven by visible light. The CAs are easily converted into their corresponding cyclic ketones without the need to use any stoichiometric activating reagents. Mechanistic studies implied that the formation of an “ate” complex from the CA and boronic acid is crucial for the generation of the acyl radical equivalent from the unreactive carboxy group.