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
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 14期
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
  • [1] Co-Catalyzed C(sp3)-C(sp2) bond cleavage via hydrogen atom transfer
    Zhou, Bingqing
    Tian, Di
    An, Jinglin
    Zhou, Yalan
    Yan, Rui
    Song, Hao
    Liu, Xiao-Yu
    Qin, Yong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (08) : 2135 - 2140
  • [2] Iron(ΙΙΙ) Catalyzed Aerobic Cα-Cβ Cleavage of Allylic Alcohols
    Bagkavou, Georgia G.
    Stathakis, Christos I.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024,
  • [3] Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C-C Bond Cleavage
    Zhang Shulin
    Zhang Zhou
    Sun Meng
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (07) : 2233 - 2240
  • [4] Palladium-Catalyzed Allylic Esterification via C-C Bond Cleavage of a Secondary Homoallyl Alcohol
    Wang, Yong
    Kang, Qiang
    [J]. ORGANIC LETTERS, 2014, 16 (16) : 4190 - 4193
  • [5] Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols
    Liu, Wei
    Wu, Qiang
    Wang, Miao
    Huang, Yahao
    Hu, Peng
    [J]. ORGANIC LETTERS, 2021, 23 (21) : 8413 - 8418
  • [6] Rhodium-Catalyzed β-Acylalkylation of Allylbenzene Derivatives with Allyl Alcohols via C-C Bond Cleavage
    Ishikawa, Soya
    Togashi, Ryo
    Ueda, Ryosuke
    Onodera, Shunsuke
    Kochi, Takuya
    Kakiuchi, Fumitoshi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05): : 3313 - 3320
  • [7] Manganese-catalyzed C-C and C-N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer
    Ansari, Mohd Farhan
    Maurya, Atul Kumar
    Kumar, Abhishek
    Elangovan, Saravanakumar
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 1111 - 1166
  • [8] Copper-Catalyzed N-Benzoylation of Amines via Aerobic C-C Bond Cleavage
    Fan, Wenyou
    Yang, Youqing
    Lei, Jianhua
    Jiang, Qijian
    Zhou, Wang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8782 - 8789
  • [9] Remote C-C bond formation via visible light photoredox-catalyzed intramolecular hydrogen atom transfer
    Chen, Hui
    Yu, Shouyun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (24) : 4519 - 4532
  • [10] Rh-catalyzed C-C bond cleavage by transfer hydroformylation
    Murphy, Stephen K.
    Park, Jung-Woo
    Cruz, Faben A.
    Dong, Vy M.
    [J]. SCIENCE, 2015, 347 (6217) : 56 - 60
12345