Blue-Light-Driven Iron-Catalyzed Desulfurization of Thioamides under Hydrosilylation Conditions

被引:0
|
作者
Zhang, Qingxin [1 ]
Darcel, Christophe [1 ]
机构
[1] Univ Rennes, CNRS, ISCR, UMR 6226, F-35000 Rennes, France
关键词
Iron; Thioamide; Desulfurization; Hydrosilylation; Blue light activation; SELECTIVE REDUCTION; ETHANETHIOL ESTERS; ACID-DERIVATIVES; TERTIARY AMIDES; ALDEHYDES; COMPLEXES; AMINATION; FACILE; AMINES; TRANSFORMATION;
D O I
10.1002/ejoc.202500048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Up to now, there were only few reports on Earth-abundant transition metal catalyzed reductions of thioamides, one of the explanation of this scarcity being the possible metallic catalyst poisoning due to the adsorption of species containing sulfur. In this contribution, we report the first general iron-catalyzed hydrogenative desulfurization of tertiary thioamides under hydrosilylation conditions at ambient temperature, the reaction being driven by blue light irradiation. To perform selectively the reduction of thioamides leading to amines (30 examples, 29-97 % yields), highlighting the sole cleavage of the C=S bond, Fe(IMes)(CO)4 catalyst was used in the presence of phenylsilane under ambient conditions.
引用
收藏
页数:6
相关论文
共 50 条
  • [21] Iron-catalyzed Hydrosilylation of Secondary Carboxamides: Chemoselective Access to Aldimines
    Wu, Jiajun
    Narayanasamy, Subash Nethaji
    Darcel, Christophe
    CHEMCATCHEM, 2023, 15 (22)
  • [22] An Iron-Catalyzed Protein Desulfurization Method Reminiscent of Aquatic Chemistry
    Desmet, Remi
    Boidin-Wichlacz, Celine
    Mhidia, Reda
    Tasiemski, Aurelie
    Agouridas, Vangelis
    Melnyk, Oleg
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (18)
  • [23] An iron-catalyzed protein desulfurization method reminiscent of aquatic chemistry
    Desmet, Remi
    Wichlacz, Celine
    Tasiemski, Aurelie
    Agouridas, Vangelis
    Melnyk, Oleg
    JOURNAL OF PEPTIDE SCIENCE, 2024, 30
  • [24] Iron-Catalyzed Stereoconvergent 1,4-Hydrosilylation of Conjugated Dienes
    Sun, Wei
    Hu, Meng-Yang
    Lu, Zhan-Sheng
    Huang, Ming-Yao
    Zhang, Xin-Yu
    Zhu, Shou-Fei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (51)
  • [25] Formamidines - Versatile Ligands for Zinc-Catalyzed Hydrosilylation and Iron-Catalyzed Epoxidation Reactions
    Enthaler, Stephan
    Schroeder, Kristin
    Inoue, Shigeyoshi
    Eckhardt, Bjoern
    Junge, Kathrin
    Beller, Matthias
    Driess, Matthias
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (25) : 4893 - 4901
  • [26] Iron-Catalyzed Asymmetric Hydrosilylation of 1,1-Disubstituted Alkenes
    Chen, Jianhui
    Cheng, Biao
    Cao, Minyi
    Lu, Zhan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (15) : 4661 - 4664
  • [27] Iron-Catalyzed Selective Hydrogenation and Hydroboration/ Hydrosilylation of CO2
    Zhao, Qiuting
    Wang, Wenguang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (10) : 3106 - 3116
  • [28] Quinoline Hydroxyalkylations from Iron-Catalyzed, Visible-Light-Driven Decarboxylations
    Rios-Malvaez, Zita G.
    Gonzalez-Rivas, Nelly
    Cuevas-Yanez, Erick
    CATALYSTS, 2024, 14 (12)
  • [29] Iron-catalyzed (E)-selective hydrosilylation of alkynes: scope and mechanistic insights
    Sen, Anirban
    Tewari, Tanuja
    Kumar, Rohit
    Vinod, C. P.
    Sharma, Himanshu
    Vanka, Kumar
    Chikkali, Samir H.
    CATALYSIS SCIENCE & TECHNOLOGY, 2024, 14 (10) : 2752 - 2760
  • [30] Iron-Catalyzed Homogeneous Hydrosilylation of Ketones and Aldehydes: Advances and Mechanistic Perspective
    Raya-Baron, Alvaro
    Ona-Burgos, Pascual
    Fernandez, Ignacio
    ACS CATALYSIS, 2019, 9 (06): : 5400 - 5417