化学
马尔科夫尼科夫法则
反应性(心理学)
亲核细胞
光催化
区域选择性
催化作用
亲核加成
电泳剂
组合化学
氧化还原
有机化学
加成反应
病理
医学
光催化
替代医学
作者
Dale J. Wilger,Jean Marc M. Grandjean,Taylor R. Lammert,David A. Nicewicz
出处
期刊:Nature Chemistry
[Springer Nature]
日期:2014-07-13
卷期号:6 (8): 720-726
被引量:239
摘要
The direct anti-Markovnikov addition of strong Bronsted acids to alkenes remains an unsolved problem in synthetic chemistry. Here, we report an efficient organic photoredox catalyst system for the addition of HCl, HF and also phosphoric and sulfonic acids to alkenes, with complete regioselectivity. These transformations were developed using a photoredox catalyst in conjunction with a redox-active hydrogen atom donor. The nucleophile counterion plays a critical role by ensuring high reactivity, with 2,6-lutidinium salts typically furnishing the best results. The nature of the redox-active hydrogen atom donor is also consequential, with 4-methoxythiophenol providing the best reactivity when 2,6-lutidinium salts are used. A novel acridinium sensitizer provides enhanced reactivity within several of the more challenging reaction manifolds. This Article demonstrates how nucleophilic addition reactions mediated by photoredox catalysis can change the way electrophilic and homofugal precursors are constructed.
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