Arenethiolate-Catalyzed 1,5-HAT of Aryl Halides: Synthesis of γ-Spirolactams

被引：5
作者：
Xiao, Wei [1 ,2 ]
Liu, Shengyun [1 ,2 ]
Lin, Yuhui [1 ,2 ]
Zhou, Xiaoyu [1 ,2 ]
Wu, Jie [1 ,2 ,3 ,4 ,5 ]
机构：
[1] Taizhou Univ, Sch Pharmaceut & Chem Engn, Taizhou 318000, Peoples R China
[2] Taizhou Univ, Inst Adv Studies, Taizhou 318000, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[4] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China
[5] Zhejiang Normal Univ, Minist Educ Adv Catalysis Mat, Key Lab, Jinhua 321004, Peoples R China
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 15期
基金：
中国国家自然科学基金;
关键词：
HYDROGEN-ATOM-TRANSFER; DERIVATIVES;
D O I：
10.1021/acs.orglett.4c00685
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
gamma-Spirolactam is a privileged building block that is found in a wide range of natural products and bioactive compounds. Herein, we report an arenethiolate-catalyzed 1,5-HAT of aryl halides to obtain gamma-spirolactams through a SET reduction/intramolecular 1,5-HAT/cyclization/HAT process. This protocol features metal-free conditions and a broad substrate scope, furnishing the gamma-spirolactams in moderate to excellent yields. Notably, aryl bromides, aryl chlorides and even aryl fluorides are well tolerated in this transformation. A mechanism involving arenethiolate as a SET catalyst is proposed based on DFT calculation.
引用
收藏
页码：3081 / 3085
页数：5
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  • [1] Thiols as Powerful Atom Transfer Catalyst: Opportunities in Photoredox-Mediated Reactions
    Bao, Xiaobo
    Yu, Wei
    Wang, Guoli
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (14) : 2299 - 2309
  • [2] Photocatalytic hydrogen atom transfer: the philosopher's stone for late-stage functionalization?
    Capaldo, Luca
    Quadri, Lorenzo Lafayette
    Ravelli, Davide
    [J]. GREEN CHEMISTRY, 2020, 22 (11) : 3376 - 3396
  • [3] Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis
    Capaldo, Luca
    Ravelli, Davide
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) : 2056 - 2071
  • [4] 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
  • [5] Photoredox-Induced Intramolecular 1,5-H Transfer Reaction of Aryl Iodides for the Synthesis of Spirocyclic γ-Lactams
    Chen, Jian-Qiang
    Chang, Rui
    Lin, Jun-Bing
    Luo, Yong-Chun
    Xu, Peng-Fei
    [J]. ORGANIC LETTERS, 2018, 20 (08) : 2395 - 2398
  • [6] Bronsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo- and Enantioselective Synthesis of Spirolactams
    Chen, Peng-Fei
    Zhou, Bo
    Wu, Peng
    Wang, Binju
    Ye, Long-Wu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (52) : 27164 - 27170
  • [7] Chiral Aryliodine-Catalyzed Asymmetric Oxidative C-N Bond Formation via Desymmetrization Strategy
    Ding, Qiang
    He, Huan
    Cai, Qian
    [J]. ORGANIC LETTERS, 2018, 20 (15) : 4554 - 4557
  • [8] Design, synthesis, and SAR of new pyrrole-oxindole progesterone receptor modulators leading to 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (WAY-255348)
    Fensome, Andrew
    Adams, William R.
    Adams, Andrea L.
    Berrodin, Tom J.
    Cohen, Jeff
    Huselton, Christine
    Illenberger, Arthur
    Kern, Jeffrey C.
    Hudak, Valerie A.
    Marella, Michael A.
    Melenski, Edward G.
    McComas, Casey C.
    Mugford, Cheryl A.
    Slayden, Ov D.
    Yudt, Matthew
    Zhang, Zhiming
    Zhang, Puwen
    Zhu, Yuan
    Winneker, Richard C.
    Wrobel, Jay E.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) : 1861 - 1873
  • [9] Exploring the applications of carbon dioxide radical anion in organic synthesis
    Gui, Yong-Yuan
    Yan, Si-Shun
    Wang, Wei
    Chen, Lin
    Zhang, Wei
    Ye, Jian-Heng
    Yu, Da-Gang
    [J]. SCIENCE BULLETIN, 2023, 68 (24) : 3124 - 3128
  • [10] Visible light photoredox-catalysed remote C-H functionalisation enabled by 1,5-hydrogen atom transfer (1,5-HAT)
    Guo, Weisi
    Wang, Qian
    Zhu, Jieping
    [J]. CHEMICAL SOCIETY REVIEWS, 2021, 50 (13) : 7359 - 7377
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