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
相关论文
共 50 条
  • [21] Amination of Benzoxazoles by Visible-Light Photoredox Catalysis
    Wang, Jia-Di
    Liu, Yu-Xia
    Xue, Dong
    Wang, Chao
    Xiao, Jianliang
    SYNLETT, 2014, 25 (14) : 2013 - 2018
  • [22] The Development of Visible-Light Photoredox Catalysis in Flow
    Garlets, Zachary J.
    Nguyen, John D.
    Stephenson, Corey R. J.
    ISRAEL JOURNAL OF CHEMISTRY, 2014, 54 (04) : 351 - 360
  • [23] Visible-light photoredox-catalyzed umpolung carboxylation of carbonyl compounds with CO2
    Cao, Guang-Mei
    Hu, Xin-Long
    Liao, Li-Li
    Yan, Si-Shun
    Song, Lei
    Chruma, Jason J.
    Gong, Li
    Yu, Da-Gang
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [24] Visible-light photoredox-catalyzed umpolung carboxylation of carbonyl compounds with CO2
    Guang-Mei Cao
    Xin-Long Hu
    Li-Li Liao
    Si-Shun Yan
    Lei Song
    Jason J. Chruma
    Li Gong
    Da-Gang Yu
    Nature Communications, 12
  • [25] Metal-free, visible-light photoredox catalysis: transformation of arylmethyl bromides to alcohols and aldehydes
    Li, Jian
    Wang, Hongni
    Liu, Li
    Sun, Jiangtao
    RSC ADVANCES, 2014, 4 (91) : 49974 - 49978
  • [26] Synthesis of β-nitro ketone by visible light photoredox catalysis
    Cao, Haoying
    Ma, Shanshan
    Yao, Yilin
    Feng, Yanhong
    Guo, Yawen
    Jiao, Peng
    CHINESE SCIENCE BULLETIN-CHINESE, 2022, 67 (20): : 2413 - 2422
  • [27] α-Alkylation of ketimines using visible light photoredox catalysis
    Franchino, Allegra
    Rinaldi, Antonia
    Dixon, Darren J.
    RSC ADVANCES, 2017, 7 (69): : 43655 - 43659
  • [28] Visible-Light Photoredox-Catalyzed Decarboxylative Alkylation of Heteroarenes Using Carboxylic Acids with Hydrogen Release
    Tian, Wan-Fa
    Hu, Chun-Hong
    He, Ke-Han
    He, Xiao-Ya
    Li, Yang
    ORGANIC LETTERS, 2019, 21 (17) : 6930 - 6935
  • [29] Intermolecular C-H Quaternary Alkylation of Aniline Derivatives Induced by Visible-Light Photoredox Catalysis
    Cheng, Jie
    Deng, Xia
    Wang, Guoqiang
    Li, Ying
    Cheng, Xu
    Li, Guigen
    ORGANIC LETTERS, 2016, 18 (18) : 4538 - 4541
  • [30] Visible-Light Photoredox Synthesis of Chiral α-Selenoamino Acids
    Jiang, Min
    Yang, Haijun
    Fu, Hua
    ORGANIC LETTERS, 2016, 18 (09) : 1968 - 1971