Synthesis of Fluorinated Imines by Addition of Fluoroalkyl Radicals to Conjugated Imines

被引:12
|
作者
Ueda, Masafumi [1 ]
Iwasada, Eri [1 ]
Miyabe, Hideto [2 ]
Miyata, Okiko [1 ]
Naito, Takeaki [1 ]
机构
[1] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan
[2] Hyogo Univ Hlth Sci, Sch Pharm, Chuo Ku, Kobe, Hyogo 6508530, Japan
来源
SYNTHESIS-STUTTGART | 2010年 / 12期
关键词
imines; fluoro compounds; addition reactions; radical reactions; fluoroalkylimines; CARBON-CENTERED RADICALS; PERFLUOROALKYL IODIDES; ASYMMETRIC-SYNTHESIS; ALKYL RADICALS; AMINO-ACIDS; TRIFLUOROMETHYLATION; CHEMISTRY; ALDEHYDES; BOND;
D O I
10.1055/s-0029-1218755
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel preparation of beta-perfluoroalkyl imine derivatives, useful as synthetic building blocks, was achieved by a route involving addition of electrophilic fluoroalkyl radicals to alpha,beta-unsaturated imines.
引用
收藏
页码:1999 / 2004
页数:6
相关论文
共 50 条
  • [11] Domino Reactions with Dicyanoalkenes and Fluorinated Conjugated Sulfinyl Imines. A Convenient Strategy for the Generation of Structural Diversity
    Gavina, Daniel
    Escolano, Marcos
    Sotorrios, Lia
    Gomez-Bengoa, Enrique
    Lopez-Ortiz, Fernando
    Sanchez-Rosello, Maria
    del Pozo, Carlos
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (04) : 970 - 981
  • [12] Functionalized α-Fluorinated Amines from Imines and Enol Ethers
    Kyrko, Dimitra
    Sarac, Murat
    Hao, Jing
    Retailleau, Pascal
    Ongeri, Sandrine
    Crousse, Benoit
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (16) : 3460 - 3465
  • [13] Regioselective Conjugate Addition of Nitriles to ,-Unsaturated Imines: Synthesis of Fluorinated Primary Enamines and 2-Aminopyridine Derivatives
    Fernandez de Troconiz, Guillermo
    Ochoa de Retana, Ana M.
    Pascual, Sergio
    Ezpeleta, Jose M.
    Palacios, Francisco
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) : 5614 - 5620
  • [14] Unexpected metal-free synthesis of trifluoromethyl arenes via tandem coupling of dicyanoalkenes and conjugated fluorinated sulfinyl imines
    Sanz-Vidal, Alvaro
    Gavina, Daniel
    Sotorrios, Lia
    Gomez-Bengoa, Enrique
    Lopez Ortiz, Fernando
    Sanchez-Rosello, Maria
    del Pozo, Carlos
    CHEMICAL COMMUNICATIONS, 2021, 57 (65) : 8023 - 8026
  • [15] Catalyzed addition of diazoacetoacetates to imines: synthesis of highly functionalized aziridines
    Zhang, Xue-jing
    Yan, Ming
    Huang, Dan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (01) : 187 - 192
  • [16] Convergent Synthesis of Piperidines by the Union of Conjugated Alkynes with Imines: A Unique Regioselective Bond Construction for Heterocycle Synthesis
    Chen, Ming Z.
    Micalizio, Glenn C.
    ORGANIC LETTERS, 2009, 11 (21) : 4982 - 4985
  • [17] Asymmetric Synthesis of α-Aminophosphonate Esters by the Addition of Dialkyl Phosphites to tert-Butanesulfinyl Imines
    Khan, Hasan A.
    Ellman, Jonathan A.
    SYNTHESIS-STUTTGART, 2013, 45 (22): : 3147 - 3150
  • [18] Addition of allylzinc to α-amino acid-derived imines: synthesis of diamino alcohols by hydroboration
    Virlouvet, Mickael
    Goesmann, Helmut
    Feldmann, Claus
    Podlech, Joachim
    MONATSHEFTE FUR CHEMIE, 2010, 141 (02): : 177 - 198
  • [19] Synthesis of N-substituted α,α-difluoro-β-aminophosphonates by addition of diethyl lithiodifluoromethylphosphonate to imines
    Cherkupally, Prabhakar
    Beier, Petr
    JOURNAL OF FLUORINE CHEMISTRY, 2012, 141 : 76 - 82
  • [20] Rhodium-Catalyzed Addition of Alkyltrifluoroborate Salts to Imines
    Lee, Sumin
    Lee, Woo Lim
    Yun, Jaesook
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2219 - 2222