烯丙基重排
化学
催化作用
三氟甲磺酸
反应性(心理学)
卤化物
钴
组合化学
反应条件
有机化学
药物化学
区域选择性
医学
替代医学
病理
作者
Henry Lindner,Erick M. Carreira
标识
DOI:10.1002/anie.202407827
摘要
We report a photochemical method for the semipinacol rearrangement of unactivated allylic alcohols. Aliphatic as well as aromatic groups participate as migrating groups, yielding a variety of α,α-disubstituted ketones. The reaction proceeds under mild conditions and is compatible with ethers, esters, halides, nitriles, carbamates, and substituted arenes. The operationally simple and fully catalytic conditions prescribe 1 mol % benzothiazinoquinoxaline as organophotocatalyst, 0.5 mol % Co-salen, and 10 mol % lutidinium triflate and, importantly, display reactivity complementary to procedures employing Brønsted acid. We showcase the utility of the protocol in late-stage drug diversifications.
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