Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China.
Org Biomol Chem. 2022 Jun 29;20(25):5104-5114. doi: 10.1039/d2ob00696k.
An Ag-catalysed three-component reaction of alkynyl aryl ketones bearing an -methoxy group, element selenium, and arylboronic acid, providing a facile route to selenofunctionalized chromone products has been developed. This protocol features high efficiency and high regioselectivity, and the use of selenium powder as the selenium source. Mechanistic experiments indicated that the combined oxidative effect of (bis(trifluoroacetoxy)iodo)benzene and oxygen in the air pushes the catalytic redox cycle of the Ag catalyst and the phenylselenium trifluoroacetate formed is the key intermediate of the PIFA-mediated 6--electrophilic cyclization and selenofunctionalization reaction of alkynyl aryl ketones.
Ag 催化的炔基芳基酮、元素硒和芳基硼酸的三组分反应，为硒官能化色酮产物提供了一种简便的方法。该方案具有高效率和高区域选择性，并且使用硒粉作为硒源。机理实验表明，(双(三氟乙酰氧基)碘)苯和空气中的氧的联合氧化作用推动了 Ag 催化剂的催化氧化还原循环，形成的苯硒三氟乙酸是 PIFA 介导的炔基芳基酮 6--亲电环化和硒官能化反应的关键中间体。
