Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of N‐Aryl α‐Amino Acids,Advanced Synthesis & Catalysis

当前位置： X-MOL 学术 › Adv. Synth. Catal. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of N‐Aryl α‐Amino Acids
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-03-09 , DOI: 10.1002/adsc.201800135
Tianju Shao ₁ , Yanli Yin _{1,

2} , Richmond Lee ₃ , Xiaowei Zhao ₁ , Guobi Chai ₄ , Zhiyong Jiang ₁

Affiliation

A visible‐light‐driven sequential photoredox catalysis to allow N‐aryl α‐amino acids to experience efficient cascade aerobic decarboxylative Povarov and oxidative dehydrogenation (ODH) reactions is described. With a dicyanopyrazine‐derived chromophore (DPZ) as a photoredox catalyst in both transformations, two series of valuable azaarenes, i. e., 4‐amino tetrahydroquinolines (THQs) and quinolines, were obtained in satisfactory yields featuring diverse 2‐ and 2,3‐substituent patterns. To enable the ODH reaction of 4‐amino THQs, a cooperative catalysis with N‐hydroxyphthalimide was developed. Additionally, an unprecedented synthesis of chiral N‐amino‐2‐methyl THQs with high enantioselectivities was realized.

中文翻译：

顺序光氧化还原催化级联好氧脱羧Povarov和N-芳基α-氨基酸的氧化脱氢反应

描述了可见光驱动的顺序光氧化还原催化，以使N-芳基α-氨基酸经历有效的级联好氧脱羧Povarov和氧化脱氢（ODH）反应。在两个转化过程中，都使用双氰基吡嗪衍生的生色团（DPZ）作为光氧化还原催化剂，得到了两个系列的有价值的氮杂芳烃，即例如，以不同的2和2,3-取代形式获得令人满意的收率的4-氨基四氢喹啉（THQs）和喹啉。为了使4-氨基THQs发生ODH反应，开发了与N-羟基邻苯二甲酰亚胺的协同催化方法。此外，实现了具有高对映选择性的手性N-氨基-2-甲基THQ的空前合成。

更新日期：2018-03-09

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11