Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines

被引:16
|
作者
Lamers, Philip [1 ]
Priebbenow, Daniel L. [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
Iron; Dealkylation; Acylation; Sulfoximines; Alkylation; OXIDATIVE AMIDATION; RECEPTOR ANTAGONIST; SULFUR IMIDATIONS; ALPHA-ARYLATION; TERTIARY-AMINES; SULFOXIMINES; METHYLATION; SULFIMIDES; PEPTIDES; ARENES;
D O I
10.1002/ejoc.201500855
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives in one pot. Subsequent cleavage of the acyl or aroyl group under acidic conditions generates a synthetically valuable NH-sulfoximine.
引用
收藏
页码:5594 / 5602
页数:9
相关论文
共 50 条
  • [1] Direct Access to N-Alkylsulfoximines from Sulfides by a Sequential Imidation/Oxidation Procedure
    Dannenberg, Carl Albrecht
    Bizet, Vincent
    Bolm, Carsten
    SYNTHESIS-STUTTGART, 2015, 47 (13): : 1951 - 1959
  • [2] Iron-Catalyzed Amidation of Aldehydes with N-Chloroamines
    Porcheddu, Andrea
    De Luca, Lidia
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2949 - 2953
  • [3] Visible-light-induced iron-catalyzed S-N cross-coupling of thiols with dioxazolones
    Tang, Jing-Jing
    Yan, Ning
    Zhang, Yiwei
    Wang, Yi
    Bao, Ming
    Yu, Xiaoqiang
    GREEN CHEMISTRY, 2023, 25 (19) : 7529 - 7533
  • [4] Iron-catalyzed C-N cross-coupling of sulfoximines with aryl iodides
    Correa, Arkaitz
    Bolm, Carsten
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) : 391 - 394
  • [5] Iron-Catalyzed N, N-formyl Ethylation of Amines
    Patel, Monak
    Sharma, Siddhant
    Bhukya, Hussain
    Dholakiya, Bharatkumar Z.
    Naveen, Togati
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (06)
  • [6] Iron-catalyzed dehydrogenative phosphonation of N,N-dimethylanilines
    Han, Wei
    Ofial, Armin R.
    CHEMICAL COMMUNICATIONS, 2009, (40) : 6023 - 6025
  • [7] Mechanochemical Iron-Catalyzed Nitrene Transfer Reactions: Direct Synthesis of N-Acyl Sulfonimidamides from Sulfinamides and Dioxazolones
    Pan, Shulei
    Mulks, Florian F.
    Wu, Peng
    Rissanen, Kari
    Bolm, Carsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (05)
  • [8] Efficient Iron-Catalyzed Reductive N-Alkylation of Aromatic Amines with Carboxylic Acid and Phenylsilane
    Qiao, Chang
    Yao, Xiang-Yang
    Liu, Xiao-Fang
    Li, Hong-Ru
    He, Liang-Nian
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (09) : 1815 - 1818
  • [9] An overview of iron-catalyzed N-alkylation reactions
    Stiniya, Sebastian
    Saranya, Padinjare Veetil
    Anilkumar, Gopinathan
    APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (12)
  • [10] Iron-catalyzed [4
    Wu, Qinghuan
    Li, Luchao
    Xu, Binyan
    Sun, Jie
    Ji, Dong
    Li, Yuguang
    Shen, Lei
    Fang, Zheng
    Duan, Jindian
    Chen, Beining
    Guo, Kai
    GREEN SYNTHESIS AND CATALYSIS, 2023, 4 (02): : 150 - 153