Rhodium-Catalyzed Cascade Carbene Coupling Reactions of α,α-Difluoro-N-Tosylhydrazones, Arylboronates and Alcohols for the Synthesis of Alkyl Enol Ethers

被引:0
|
作者
Zhao, Yueting [1 ]
Wang, Xu [1 ]
Li, Ran [1 ]
Wang, Bingxue [1 ]
Gao, Kefu [1 ]
Wei, Pifeng [1 ]
Hu, Fangdong [1 ]
机构
[1] Linyi Univ, Sch Chem & Chem Engn, Linyi 276000, Peoples R China
关键词
alpha; alpha-difluoro-N-tosylhydrazone; carbene; cascade reaction; rhodium catalysis; alkyl enol ether; HALO-N-TOSYLHYDRAZONES; METAL; CONSTRUCTION; REAGENTS; INDOLES;
D O I
10.1002/ejoc.202401445
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Transition metal-catalyzed cascade carbene coupling reactions are highly valued strategies for the assembly of complex molecules. Among various carbene precursors, alpha,alpha-difluoro-N-tosylhydrazones have emerged as promising candidates in such reactions. In this study, we report a rhodium-catalyzed three-component carbene coupling reaction involving alpha,alpha-difluoro-N-tosylhydrazones, arylboronates and alcohols. This approach provides a complementary method for the efficient synthesis of alkyl enol ethers, showcasing a broad substrate scope and favorable yields. Additionally, the subsequent transformations of the resulting products demonstrate the synthetic utility and versatility of this protocol.
引用
收藏
页数:6
相关论文
共 50 条
  • [21] Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Ethers: Enantioselective Synthesis of Diarylethanes
    Taylor, Buck L. H.
    Swift, Elizabeth C.
    Waetzig, Joshua D.
    Jarvo, Elizabeth R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (03) : 389 - 391
  • [22] Rhodium-Catalyzed Cascade Reactions of Indoles with 4-Hydroxy-2-Alkynoates for the Synthesis of Indole-Fused Polyheterocycles
    Wu, Xiaowei
    Li, Pinyi
    Lu, Yangbin
    Qiao, Jin
    Zhao, Jingwei
    Jia, Xiuwen
    Ni, Hangcheng
    Kong, Lichun
    Zhang, Xiaoning
    Zhao, Fei
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) : 2953 - 2960
  • [23] Enantioselective Rhodium-Catalyzed Arylation of Cyclic N-Sulfamidate Alkylketimines: A New Access to Chiral β-Alkyl-β-aryl Amino Alcohols
    Chen, Ya-Jing
    Chen, Ya-Heng
    Feng, Chen-Guo
    Lin, Guo-Qiang
    ORGANIC LETTERS, 2014, 16 (12) : 3400 - 3403
  • [24] Rhodium(III)-Catalyzed Cascade C-H Activation/Annulation of N-carbamoylindoles with Silyl Enol Ethers for the Construction of Dihydropyrimidoindolone Skeletons
    Chen, Lu
    Wang, Zhichao
    Pang, Binghan
    Wang, Yangyang
    Xu, Xiaobo
    Wu, Gaorong
    Ji, Yafei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (10) : 2603 - 2610
  • [25] Efficient Synthesis of Eight-Membered Nitrogen Heterocycles from O-Propargylic Oximes by Rhodium-Catalyzed Cascade Reactions
    Nakamura, Itaru
    Sato, Yoshinori
    Takeda, Keisuke
    Terada, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (33) : 10214 - 10219
  • [26] Rhodium-Catalyzed [3+2]-Annulation of ortho-Diazoquinones with Enol Ethers: Diversity-Oriented Total Synthesis of Aflatoxin B2
    Paymode, Dinesh J.
    Sharma, Indrajeet
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (13) : 2034 - 2040
  • [27] ASYMMETRIC HYDROGENATION OF ENOL PHOSPHINATES CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-RHODIUM COMPLEX - ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE SECONDARY ALKYL ALCOHOLS
    HAYASHI, T
    KANEHIRA, K
    KUMADA, M
    TETRAHEDRON LETTERS, 1981, 22 (44) : 4417 - 4420
  • [28] TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS, EFFICIENT SYNTHESIS OF FUNCTIONALIZED ETHERS BY CARBENE INSERTION INTO THE HYDROXYLIC BOND OF ALCOHOLS
    NOELS, AF
    DEMONCEAU, A
    PETINIOT, N
    HUBERT, AJ
    TEYSSIE, P
    TETRAHEDRON, 1982, 38 (17) : 2733 - 2739
  • [29] Nickel catalyzed dealkoxylative Csp2-Csp3 cross coupling reactions - stereospecific synthesis of allylsilanes from enol ethers
    Guo, Lin
    Leiendecker, Matthias
    Hsiao, Chien-Chi
    Baumann, Christoph
    Rueping, Magnus
    CHEMICAL COMMUNICATIONS, 2015, 51 (10) : 1937 - 1940
  • [30] Rhodium-catalyzed carbonylation of allylaminoalcohols: Catalytic synthesis of N-(2-hydroxy-alkyl)-gamma-lactams and bicyclic oxazolidines
    Limberger, J.
    Mottin, M.
    Nachtigall, F. F.
    Castellano, E. E.
    da Rosa, R. G.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 294 (1-2) : 82 - 92