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

被引：2
|
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
  • [31] Photoredox catalysis in nickel-catalyzed C-H functionalization
    Mantry, Lusina
    Maayuri, Rajaram
    Kumar, Vikash
    Gandeepan, Parthasarathy
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 2209 - 2259
  • [32] Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis
    Chatterjee, Tanmay
    Iqbal, Naeem
    You, Youngmin
    Cho, Eun Jin
    ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) : 2284 - 2294
  • [33] Visible-Light Photoredox-Catalyzed α-Regioselective Conjugate Addition of Allyl Groups to Activated Alkenes
    Gontala, Arjun
    Woo, Sang Kook
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (15) : 3223 - 3228
  • [34] Direct Transformation of Nitroalkanes to Nitriles Enabled by Visible-Light Photoredox Catalysis and a Domino Reaction Process
    Li, Yu-Hsun
    Akula, Pavan Sudheer
    Hong, Bor-Cherng
    Peng, Chieh-Hung
    Lee, Gene-Hsiang
    ORGANIC LETTERS, 2019, 21 (19) : 7750 - 7754
  • [35] Merging Visible-Light-Photoredox and Nickel Catalysis
    Vila, Carlos
    CHEMCATCHEM, 2015, 7 (12) : 1790 - 1793
  • [36] Visible-light photoredox catalyzed oxidative Strecker reaction
    Rueping, Magnus
    Zhu, Shaoqun
    Koenigs, Rene M.
    CHEMICAL COMMUNICATIONS, 2011, 47 (47) : 12709 - 12711
  • [37] Visible-Light Photoredox Catalyzed Decarboxylative Alkylation of Vinylcyclopropanes
    Chandu, Palasetty
    Das, Debabrata
    Ghosh, Krishna G.
    Sureshkumar, Devarajulu
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) : 2340 - 2345
  • [38] Photoredox-Catalysis-Modulated, Nickel-Catalyzed Divergent Difunctionalization of Ethylene
    Li, Jiesheng
    Luo, Yixin
    Cheo, Han Wen
    Lan, Yu
    Wu, Jie
    CHEM, 2019, 5 (01): : 192 - 203
  • [39] Benzylic functionalization via visible-light induced photoredox catalysis
    Xing, Yalan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [40] Visible-Light Photoredox and Palladium Dual Catalysis in Organic Synthesis
    Zhou, Wenjun
    Jiang, Yuanxu
    Chen, Liang
    Liu, Kaixing
    Yu, Dagang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (11) : 3697 - 3713
12345