In situ generation of radical initiators using amine-borane complexes for carbohalogenation of alkenes

被引:7
|
作者
Liautard, Virginie [1 ]
Delgado, Marine [1 ,2 ]
Colin, Boris [2 ]
Chabaud, Laurent [1 ]
Michaud, Guillaume [2 ]
Pucheault, Mathieu [1 ]
机构
[1] Univ Bordeaux, ISM, Bordeaux INP, CNRS,UMR 5255, F-33400 Talence, France
[2] ZAC Bois Plaisance, BOSTIK, Smart Technol Ctr, 101 Rue Champ Cailloux, F-60280 Venette, France
关键词
MOLECULAR ADDITION-COMPOUNDS; HOMOLYTIC REACTIONS; LIGATED BORANES; TRIETHYLBORANE; CYCLIZATION; REAGENT;
D O I
10.1039/d1cc06390a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Atom transfer radical addition of alkyl halides to alkenes was developed using a low amount of a stable initiator, amine borane complexes. Thanks to a slow hydroboration step, the overall carbohalogenation process leads to good isolated yields.
引用
收藏
页码:2124 / 2127
页数:4
相关论文
共 50 条
  • [1] Synthesis and Comparison of Reactivity of Amine-Borane Complexes
    Jayakumar, S. venkatesan
    Tomar, Divya rana
    ORIENTAL JOURNAL OF CHEMISTRY, 2024, 40 (06) : 1709 - 1714
  • [2] On the Use of Amine-Borane Complexes To Synthesize Iron Nanoparticles
    Pelletier, Frederic
    Ciuculescu, Diana
    Mattei, Jean-Gabriel
    Lecante, Pierre
    Casanove, Marie-Jose
    Yaacoub, Nader
    Greneche, Jean-Marc
    Schmitz-Antoniak, Carolin
    Amiens, Catherine
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (19) : 6021 - 6026
  • [3] Amine-borane complex-initiated SF5Cl radical addition on alkenes and alkynes
    Gilbert, Audrey
    Langowski, Pauline
    Delgado, Marine
    Chabaud, Laurent
    Pucheault, Mathieu
    Paquin, Jean-Francois
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 3069 - 3077
  • [4] Metallation of benzylic amines via amine-borane complexes
    Ebden, MR
    Simpkins, NS
    Fox, DNA
    TETRAHEDRON, 1998, 54 (42) : 12923 - 12952
  • [5] DFT investigation on dihydrogen-bonded amine-borane complexes
    Yan, Shihai
    Zou, Hongmei
    Kang, Wukui
    Sun, Lixiang
    JOURNAL OF MOLECULAR MODELING, 2016, 22 (01) : 1 - 10
  • [6] DFT investigation on dihydrogen-bonded amine-borane complexes
    Shihai Yan
    Hongmei Zou
    Wukui Kang
    Lixiang Sun
    Journal of Molecular Modeling, 2016, 22
  • [7] Amine-Borane σ-Complexes of Rhodium. Relevance to the Catalytic Dehydrogenation of Amine-Boranes
    Douglas, Thomas M.
    Chaplin, Adrian B.
    Weller, Andrew S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) : 14432 - +
  • [8] Chiral intramolecular amine-borane complexes as reducing agents for prochiral ketones
    Le, Toumelin, J.-B.
    Baboulene, M.
    Tetrahedron: Asymmetry, 8 (08):
  • [9] Direct Experimental Observation of in situ Dehydrogenation of an Amine-Borane System Using Gas Electron Diffraction
    Ja'o, Aliyu M.
    Masters, Sarah L.
    Wann, Derek A.
    Rankine, Conor D.
    Nunes, Joao P. F.
    Guillemin, Jean-Claude
    JOURNAL OF PHYSICAL CHEMISTRY A, 2019, 123 (32): : 7104 - 7112
  • [10] Chiral intramolecular amine-borane complexes as reducing agents for prochiral ketones
    LeToumelin, JB
    Baboulene, M
    TETRAHEDRON-ASYMMETRY, 1997, 8 (08) : 1259 - 1265