Aerobic C-C Bond Cleavage of Allylic Alcohols via Co-Catalyzed Hydrogen Atom Transfer

被引:2
|
作者
Deng, Meng [1 ]
Chu, Mengqi [2 ]
Li, Nan [2 ]
Sun, Guohui [1 ]
Li, Fei [1 ]
Guo, Dade [2 ]
Kang, Guohui [2 ]
Ji, Baoming [2 ]
机构
[1] Luoyang Normal Univ, Coll Food & Drug, Luoyang Key Lab Organ Funct Mol, Luoyang 471934, Henan, Peoples R China
[2] Luoyang Normal Univ, Coll Chem & Chem Engn, Henan Key Lab Funct Oriented Porous Mat, Luoyang 471934, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
MOLECULAR-OXYGEN; ENANTIOSPECIFIC SYNTHESIS; FRAGMENTATION; ALKENES; OLEFINS; FE;
D O I
10.1021/acs.orglett.3c00556
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, efficient method has been developed for the Co-III-H-catalyzed aerobic C-C bond cleavage of tertiary allylic alcohols to access ketones. This novel approach presents excellent chemoselectivity, good functional group compatibility, and high yields. This reaction occurs through a HAT-initiated peroxide intermediate, and an adjacent glycol-type diradical fragmentation process is recommended.
引用
收藏
页码:2420 / 2425
页数:6
相关论文
共 50 条
  • [21] Efficient Vanadium-Catalyzed Aerobic C-C Bond Oxidative Cleavage of Vicinal Diols
    Amadio, Emanuele
    Gonzalez-Fabra, Joan
    Carraro, Davide
    Denis, William
    Gjoka, Blerina
    Zonta, Cristiano
    Bartik, Kristin
    Cavani, Fabrizio
    Solmi, Stefania
    Bo, Carles
    Licini, Giulia
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (17) : 3286 - 3296
  • [22] Electrochemical oxidative C-C bond cleavage of methylenecyclopropanes with alcohols
    Kumar, Rakesh
    Dutt, Shiv
    Banerjee, Prabal
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (31) : 4246 - 4249
  • [23] Vanadium-catalyzed isomerization of cyclopropanemethanols to homoallylic alcohols involving C-C bond cleavage
    Maeda, Y
    Nishimura, T
    Uemura, S
    [J]. CHEMISTRY LETTERS, 2005, 34 (03) : 380 - 381
  • [24] Aerobic oxidative α-arylation of furans with boronic acids via Pd(II)-catalyzed C-C bond cleavage of primary furfuryl alcohols: sustainable access to arylfurans
    Huang, Guanghao
    Lu, Lin
    Jiang, Huanfeng
    Yin, Biaolin
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (90) : 12217 - 12220
  • [25] Thermal decomposition of alkenes: role of allylic C-C bond cleavage
    Liu, Dapeng
    Farooq, Aamir
    [J]. COMBUSTION AND FLAME, 2024, 268
  • [26] Copper-Catalyzed Aza-Benzyl Transfer Michael Addition via C-C Bond Cleavage
    Xiong, Si-Qi
    Hong, Chuan-Ming
    Li, Qing-Hua
    Liu, Tang -Lin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06): : 3523 - 3531
  • [27] CLEAVAGE OF C-C BOND ACTIVATED BY H-ATOM
    AMANO, A
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 104 - 104
  • [28] Base-catalyzed synthesis of amides and imines via C-C and C=C bond cleavage
    Yadav, Dilip Kumar T.
    Bhanage, Bhalchandra M.
    [J]. RSC ADVANCES, 2015, 5 (16) : 12387 - 12391
  • [29] Copper-Catalyzed Methyl Esterification Reactions via C-C Bond Cleavage
    Zhu, Yan
    Yan, Hong
    Lu, Linhua
    Liu, Defu
    Ron, Guangwei
    Mao, Jincheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19): : 9898 - 9905
  • [30] Alkenyl Exchange of Allylamines via Nickel(0)-Catalyzed C-C Bond Cleavage
    Fan, Chao
    Lv, Xin-Yang
    Xiao, Li-Jun
    Xie, Jian-Hua
    Zhou, Qi-Lin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (07) : 2889 - 2893