Phosphonylacylation of Alkenes Enabled by Visible-Light-Induced N-Heterocyclic Carbene Catalysis

被引：3
|
作者：
Jin, Ming-Lei [1 ,2 ]
Dong, Yi-Xiong [1 ,2 ]
Gao, Zhong-Hua [1 ,2 ]
Ye, Song [1 ,2 ]
机构：
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 08期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1021/acs.orglett.4c00242
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report the phosphonylacylation of alkenes via visible-light-induced N-heterocyclic carbene (NHC) catalysis to afford a series of gamma-ketophosphonates in moderate to good yields. This protocol features mild conditions, free of photocatalyst, and good compatibility of functional groups. The excited Breslow enolate intermediate was proposed to undergo single-electron transfer with oxime phosphonate to generate the corresponding ketyl radical and phosphonyl radical.
引用
收藏
页码：1711 / 1717
页数：7
相关论文
共 50 条
  • [21] New frontiers of N-heterocyclic carbene catalysis
    Jiean Chen
    Yong Huang
    Science China(Chemistry), 2016, (03) : 251 - 254
  • [22] Copper N-heterocyclic carbene complexes in catalysis
    Egbert, Jonathan D.
    Cazin, Catherine S. J.
    Nolan, Steven P.
    CATALYSIS SCIENCE & TECHNOLOGY, 2013, 3 (04) : 912 - 926
  • [23] Supported N-heterocyclic carbene complexes in catalysis
    Sommer, William J.
    Weck, Marcus
    COORDINATION CHEMISTRY REVIEWS, 2007, 251 (5-6) : 860 - 873
  • [24] New advances in N-heterocyclic carbene catalysis
    Scheidt, Karl A.
    Chan, Audrey
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [25] New frontiers of N-heterocyclic carbene catalysis
    Jiean Chen
    Yong Huang
    Science China Chemistry, 2016, 59 : 251 - 254
  • [26] New frontiers of N-heterocyclic carbene catalysis
    Chen, Jiean
    Huang, Yong
    SCIENCE CHINA-CHEMISTRY, 2016, 59 (03) : 251 - 254
  • [27] Smart N-Heterocyclic Carbene Ligands in Catalysis
    Peris, Eduardo
    CHEMICAL REVIEWS, 2018, 118 (19) : 9988 - 10031
  • [28] Visible-Light-Induced Aminochlorination of Alkenes
    Mejri, Emna
    Higashida, Kosuke
    Kondo, Yuta
    Nawachi, Anna
    Morimoto, Hiroyuki
    Ohshima, Takashi
    Sawamura, Masaya
    Shimizu, Yohei
    ORGANIC LETTERS, 2023, 25 (24) : 4581 - 4585
  • [29] Aerobic oxidative N-heterocyclic carbene catalysis
    Stenkvist, Simon
    Bacaicoa, Sara
    Goossens, Ellymay
    Sunden, Henrik
    CHEMICAL RECORD, 2023, 23 (07):
  • [30] Visible-light-induced hydroalkoxymethylation of electron-deficient alkenes by photoredox catalysis
    Miyazawa, Kazuki
    Yasu, Yusuke
    Koike, Takashi
    Akita, Munetaka
    CHEMICAL COMMUNICATIONS, 2013, 49 (65) : 7249 - 7251
12345