Reductive amination with zinc borohydride. Efficient, safe route to fluorinated benzylamines

被引:53
作者
Bhattacharyya, S [1 ]
Chatterjee, A [1 ]
Williamson, JS [1 ]
机构
[1] UNIV MISSISSIPPI,SCH PHARM,DEPT MED CHEM,UNIVERSITY,MS 38677
关键词
D O I
10.1080/00397919708005050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fluorinated benzylamines are synthesized in high yields by reductive alkylation of secondary amines with appropriate fluoroaldehydes using a combination of zinc chloride and zinc borohydride. The present method offers an alternative to toxic sodium cyanoborohydride and is adaptable to multigram-scale preparations.
引用
收藏
页码:4265 / 4274
页数:10
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  • [1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
    AbdelMagid, AF
    Carson, KG
    Harris, BD
    Maryanoff, CA
    Shah, RD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3849 - 3862
  • [2] ABDELMAGID AF, 1990, SYNLETT, P537
  • [3] AbdelMagid AF, 1996, ACS SYM SER, V641, P201
  • [4] REDUCTIVE AMINATION OF ALDEHYDES AND KETONES BY USING SODIUM TRIACETOXYBOROHYDRIDE
    ABDELMAGID, AF
    MARYANOFF, CA
    CARSON, KG
    [J]. TETRAHEDRON LETTERS, 1990, 31 (39) : 5595 - 5598
  • [5] [Anonymous], 1991, Fluorine in Bioorganic Chemistry
  • [6] HIGHLY DIASTEREOSELECTIVE ALKYLATIONS OF CHIRAL AMIDE ENOLATES - NEW ROUTES TO HYDROXYETHYLENE DIPEPTIDE ISOSTERE INHIBITORS OF HIV-1 PROTEASE
    ASKIN, D
    WALLACE, MA
    VACCA, JP
    REAMER, RA
    VOLANTE, RP
    SHINKAI, I
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) : 2771 - 2773
  • [7] Banks R.E., 1994, ORGANOFLUORINE CHEM
  • [8] BARNEY CL, 1990, TETRAHEDRON LETT, V39, P5547
  • [9] BHATTACHARYYA S, 1995, SYNLETT, P971
  • [10] Simple reduction of ferrocenyl aldehydes and ketones by sodium boranuide in trifluoroacetic acid: New, efficient, general preparation of alkylferrocenes
    Bhattacharyya, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12): : 1381 - 1383