Visible-Light Photoredox Enables Ketone Carbonyl Alkylation for Easy Access to Tertiary Alcohols

被引:35
|
作者
Minh Duy Vu [1 ]
Das, Mrinmoy [1 ]
Guo, Aoxin [1 ]
Ang, Zi-En [1 ]
Dokic, Milos [1 ]
Soo, Han Sen [1 ]
Liu, Xue-Wei [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore
基金
新加坡国家研究基金会;
关键词
photoredox catalysis; HAT catalyst; ketyl radical; tertiary alcohol; radical-radical cross coupling; C-H BONDS; COUPLED ELECTRON-TRANSFER; DIRECT ARYLATION; ACTIVATION; CATALYSIS; FUNCTIONALIZATION; ALDEHYDES; HALIDES; MERGER;
D O I
10.1021/acscatal.9b02401
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Being a handle for synthesizing quaternary carbon centers and olefins, together with ubiquitous appearance in organic building blocks, makes tertiary alcohols valuable targets in synthesis. However, traditional syntheses of these alcohols have faced several challenges including the employment of functionalized reactive reagents, undesirable side reactions, and decomposition of the alcohol products under harsh conditions. The paucity of a synthetic approach to bulky tertiary alcohols prompts our interest to develop a benign catalytic protocol to tackle the current issues. Here, we have successfully demonstrated the use of ketyl radicals in intermolecular cross radical-radical coupling, which has opened a different door for accessing complex tertiary alcohols. On the other hand, by starting from feedstock and naturally derived chemicals without any pre-activation, it would be superior to traditional methodologies in the industrial context.
引用
收藏
页码:9009 / 9014
页数:11
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