Synthesis of gem-Difluoroalkenes via a Sequence of Hydroboration and 1,2-Elimination of α,β-Unsaturated Carbonyls

被引:5
|
作者
An, Shiyun [1 ,2 ]
Zhang, Jinlong [1 ]
Jiang, Gaoxi [1 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys LICP, Suzhou Res Inst LICP, Ctr Excellence Mol Synth,State Key Lab Oxo Synth, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
关键词
gem-difluoroalkene; boration; 1,2-elimination; alpha; beta-unsaturated carbonyls; fluoroalkene; DIFLUOROMETHYL 2-PYRIDYL SULFONE; CROSS-COUPLING REACTIONS; FUNCTIONALIZED 1,1-DIFLUORO-1-ALKENES; ORGANOLITHIUM REAGENTS; EFFICIENT APPROACH; CONCISE SYNTHESIS; DIFLUOROOLEFINATION; DIFLUOROCARBENE; INHIBITORS; ALDEHYDES;
D O I
10.1055/s-0040-1707311
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We reported a simple protocol for the synthesis ofgem-difluoroalkenes via a reaction sequence of hydroboration and 1,2-elimination of alpha,beta-unsaturated carbonyl substrates under mild conditions. Two steps of this method could be executed in one pot. The beta-CF2H- and beta-CFH2-alpha,beta-unsaturated carbonyls can be obtained smoothly from the alpha,beta-unsaturatedgem-difluoroamide with NaH as the base and via a boration-1,2-elimination sequence.
引用
收藏
页码:91 / 94
页数:4
相关论文
共 50 条
  • [31] Tunable Synthesis of Monofluoroalkenes and Gem-Difluoroalkenes via Solvent-Controlled Rhodium-Catalyzed Arylation of 1-Bromo-2,2-difluoroethylene
    Xu, Wen-Yan
    Xu, Zhe-Yuan
    Zhang, Ze-Kuan
    Gong, Tian-Jun
    Fu, Yao
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023,
  • [32] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Reductive C-F and C-O Bond Cleavage
    Lin, Zhiyang
    Lan, Yun
    Wang, Chuan
    [J]. ACS CATALYSIS, 2019, 9 (01) : 775 - 780
  • [33] AZIRIDINE-AZIRINE TRANSFORMATION BY 1,2-ELIMINATION VIA AN AZIRIDINYL CARBANION INTERMEDIATE
    ATKINSON, RS
    KELLY, BJ
    [J]. TETRAHEDRON LETTERS, 1989, 30 (20) : 2703 - 2704
  • [34] Stereoselective Synthesis of Difluorinated 1,3-Dienes via Palladium-Catalyzed C-F Bond Activation of Tetrasubstituted gem-Difluoroalkenes
    Wang, Yanhui
    Ma, Qiao
    Tsui, Gavin Chit
    [J]. ORGANIC LETTERS, 2021, 23 (13) : 5241 - 5245
  • [35] Tunable Synthesis of Monofluoroalkenes and Gem-Difluoroalkenes via Solvent-Controlled Rhodium-Catalyzed Arylation of 1-Bromo-2,2-difluoroethylene
    Xu, Wen-Yan
    Xu, Zhe-Yuan
    Zhang, Ze-Kuan
    Gong, Tian-Jun
    Fu, Yao
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (40)
  • [36] An 1,2-Elimination Approach to the Enantioselective Synthesis of 1,3-Disubstituted Linear Allenes
    Zhang, Yan
    Hao, Hong-Dong
    Wu, Yikang
    [J]. SYNLETT, 2010, (06) : 905 - 908
  • [37] Cross-Electrophile Coupling between Aryl/Vinyl Triflates and Vinyl Tosylates for the Synthesis of gem-Difluoroalkenes via Ni/Pd Cooperative Catalysis
    Xiong, Baojian
    Li, Yue
    Zhang, Jinyu
    Liu, Jiangjun
    Zhang, Xuemei
    Lian, Zhong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (05) : 1009 - 1015
  • [38] Indolizine synthesis via copper-catalyzed cyclization of gem-difluoroalkenes and 2-(pyridin-2-yl)acetate derivatives
    Lu, Chuan-Jun
    Yu, Xin
    Chen, Yu-Ting
    Song, Qing-Bao
    Wang, Hong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (16): : 2313 - 2318
  • [39] N-Directed defluorinative γ-C(sp3)-H allylation of sulfamate esters for synthesis of gem-difluoroalkenes via photoredox catalysis
    Yang, Jia-Wen
    Li, Meng
    Tan, Guang-Qiang
    Liu, Feng
    Qin, Hai-Tao
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (17)
  • [40] Ring-fluorinated naphthalene and indene synthesis via 6-and 5-endo-trig cyclizations of gem-difluoroalkenes by carbon nucleophiles
    Ichikawa, J
    Miyazaki, H
    Sakoda, K
    Wada, Y
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (04) : 585 - 593