Redox-Neutral Decarboxylative and Desulfonylative C(sp3) Trifluoromethylation: Method Development and Mechanistic Inquiry

被引:2
|
作者
Seong, Chris M. [1 ]
Roberts, Courtney C. [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 89卷 / 22期
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
MEDIATED TRIFLUOROMETHYLATION; RADICALS; FLUORINE; DISCOVERY; ALKENES; ALKYL;
D O I
10.1021/acs.joc.3c00872
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sodium triflinate (CF3SO2Na) isan inexpensivebench-stable radical CF3 source that is often activatedby external oxidants such as peroxides. However, despite the commercialaccessibility of CF3SO2Na, the salt has neverbeen applied to decarboxylative trifluoromethylation due to challengesin controlled cross-radical coupling. We report a redox-neutral approachto decarboxylative C(sp(3)) trifluoromethylation of carboxylicacid derivatives. Mechanistic inquiry is performed to address thelimitations in scope.
引用
收藏
页码:16114 / 16120
页数:7
相关论文
共 50 条
  • [31] Cu/photoredox-catalyzed decarboxylative radical C(sp3)–C(sp3)cross-coupling reactions
    Chao Jiang
    Pinhong Chen
    Guosheng Liu
    Science China(Chemistry), 2023, (10) : 2858 - 2862
  • [32] Functionalization of an sp3 C-H bond via a redox-neutral domino reaction: diastereoselective synthesis of hexahydropyrrolo[2,1-b]oxazoles
    Rahman, Matiur
    Bagdi, Avik Kumar
    Mishra, Subhajit
    Hajra, Alakananda
    CHEMICAL COMMUNICATIONS, 2014, 50 (22) : 2951 - 2953
  • [33] Trifluoromethylation of Carbonyl and Unactivated Olefin Derivatives by C(sp3)-C Bond Cleavage
    Cong, Fei
    Mega, Riccardo S.
    Chen, Jinhong
    Day, Craig S.
    Martin, Ruben
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (15)
  • [34] Merging photoredox with metalloenzymatic catalysis for enantioselective decarboxylative C(sp3)-N3 and C(sp3)-SCN bond formation
    Rui, Jinyan
    Mu, Xinpeng
    Soler, Jordi
    Paris, Jared C.
    Guo, Yisong
    Garcia-Borras, Marc
    Huang, Xiongyi
    NATURE CATALYSIS, 2024, 7 (12): : 1394 - 1403
  • [35] Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies
    Shekhar, K. C.
    Dhungana, Roshan K.
    Shrestha, Bijay
    Thapa, Surendra
    Khanal, Namrata
    Basnet, Prakash
    Lebrun, Robert W.
    Giri, Ramesh
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (31) : 9801 - 9805
  • [36] Copper-Catalyzed C(sp3)-C(sp3) Bond Formation Using a Hypervalent Iodine Reagent: An Efficient Allylic Trifluoromethylation
    Wang, Xi
    Ye, Yuxuan
    Zhang, Songnan
    Feng, Jiajie
    Xu, Yan
    Zhang, Yan
    Wang, Jianbo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) : 16410 - 16413
  • [37] Redox-Neutral Ni-Catalyzed sp3C-H Alkylation ofα-Olefins withUnactivated Alkyl Bromides
    Buendia, Mikkel B.
    Higginson, Bradley
    Kegnaes, Soren
    Kramer, Soren
    Martin, Ruben
    ACS CATALYSIS, 2022, 12 (07) : 3815 - 3820
  • [38] Photoelectrocatalyzed Alkylation of Phosphonites by Direct Decarboxylative C(sp3)-P Coupling
    Yuan, Kang-Ning
    Xie, Tian
    Wang, Jia-Bao
    Wang, Dali
    Shang, Ming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [39] Organophotoredox-Catalyzed Decarboxylative C(sp3)-O Bond Formation
    Shibutani, Shotaro
    Kodo, Taiga
    Takeda, Mitsutaka
    Nagao, Kazunori
    Tokunaga, Norihito
    Sasaki, Yusuke
    Ohmiya, Hirohisa
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (03) : 1211 - 1216
  • [40] Mechanistic investigation into the C( sp3)- H acetoxylation of morpholinones
    Buettner, Cornelia S.
    Willcox, Darren
    Chappell, Ben. G. N.
    Gaunt, Matthew J.
    CHEMICAL SCIENCE, 2019, 10 (01) : 83 - 89