Nickel-Catalyzed Regioselective Hydrothiolation of Allenes Enabled by Visible-Light Photoredox Catalysis

被引：0
|
作者：
Xie, Hui [1 ]
Breit, Bernhard [1 ]
机构：
[1] Albert Ludwigs Univ Freiburg, Inst Organ Chem, D-79104 Freiburg, Germany
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 21期
关键词：
S BOND FORMATION; SELECTIVE HYDROTHIOLATION; SYNTHETIC ASPECTS; ALKYNES; SULFUR; ALLYLATION;
D O I：
10.1021/acs.orglett.4c01027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hydrothiolation presents an attractive way to transform allenes into allylic thioethers. Herein, we described an efficient visible-light photoredox-promoted nickel-catalyzed hydrothiolation of allenes with functionalized aromatic and aliphatic thiols. This synergistic catalytic system exhibits unprecedentedly high reactivities and regiocontrol for the construction of allylic thioethers, representing the unique synthetic utility of the earth-abundant Ni-catalyzed method compared with the related noble-metal-catalyzed allylation reactions.
引用
收藏
页码：4438 / 4442
页数：5
相关论文
共 50 条
  • [21] Access to branched allylsilanes by nickel-catalyzed regioselective hydrosilylation of allenes
    Zeng, Jia-Hao
    Chen, Jun-Jia
    Chen, Li
    Zhan, Zhuang-Ping
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (09) : 1132 - 1136
  • [22] Decarboxylative Alkynylation and Carbonylative Alkynylation of Carboxylic Acids Enabled by Visible-Light Photoredox Catalysis
    Zhou, Quan-Quan
    Guo, Wei
    Ding, Wei
    Wu, Xiong
    Chen, Xi
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (38) : 11196 - 11199
  • [23] PQS-enabled visible-light iridium photoredox catalysis in water at room temperature
    Bu, Mei-Jie
    Cai, Chun
    Gallou, Fabrice
    Lipshutz, Bruce H.
    GREEN CHEMISTRY, 2018, 20 (06) : 1233 - 1237
  • [24] General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis
    Guo, Lei
    Yuan, Mingbin
    Zhang, Yanyan
    Wang, Fang
    Zhu, Shengqing
    Gutierrez, Osvaldo
    Chu, Lingling
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (48) : 20390 - 20399
  • [25] Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N-C Cleavage of Imides
    Amani, Javad
    Alam, Rauful
    Badir, Shorouk
    Molander, Gary A.
    ORGANIC LETTERS, 2017, 19 (09) : 2426 - 2429
  • [26] Dicarboxylation of alkenes, allenes and (hetero)arenes with CO2 via visible-light photoredox catalysis
    Tao Ju
    Yu-Qin Zhou
    Ke-Gong Cao
    Qiang Fu
    Jian-Heng Ye
    Guo-Quan Sun
    Xiao-Feng Liu
    Li Chen
    Li-Li Liao
    Da-Gang Yu
    Nature Catalysis, 2021, 4 : 304 - 311
  • [27] Dicarboxylation of alkenes, allenes and (hetero)arenes with CO2 via visible-light photoredox catalysis
    Ju, Tao
    Zhou, Yu-Qin
    Cao, Ke-Gong
    Fu, Qiang
    Ye, Jian-Heng
    Sun, Guo-Quan
    Liu, Xiao-Feng
    Chen, Li
    Liao, Li-Li
    Yu, Da-Gang
    NATURE CATALYSIS, 2021, 4 (04) : 304 - 311
  • [28] Visible-Light Photoredox Catalysis in Natural Products Synthesis
    Tan Fen
    Xiao Wenjing
    ACTA CHIMICA SINICA, 2015, 73 (02) : 85 - 89
  • [29] Highly enantioselective and regioselective nickel-catalyzed coupling of allenes, aldehydes, and silanes
    1600, American Chemical Society, Columbus, United States (127):
  • [30] Highly enantioselective and regioselective nickel-catalyzed coupling of allenes, aldehydes, and silanes
    Ng, SS
    Jamison, TF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) : 7320 - 7321
12345