Reductive Amination with Zinc Borohydride. Efficient, Safe Route to Fluorinated Benzylamines

References

• Sheppard , W. A. and Sharts , C. M. 1969 . Organic Fluorine Chemistry , New York : Benjamin .
   Google Scholar
• Schlosser , M. 1978 . Tetrahedron , 34 : 3
   Web of Science ®Google Scholar
• Purrington , S. T. , Kagan , B. S. and Patrick , T. B. 1986 . Chem. Rev. , 86 : 997
   Web of Science ®Google Scholar
• Rozen , S. 1988 . Acc. Chem. Res. , 21 : 307
   Web of Science ®Google Scholar
• Walba , D. M. , Razavi , H. A. , Clark , N. A. and Parmar , D. S. 1988 . J. Am. Chem. Soc. , 110 : 8686
   Web of Science ®Google Scholar
• Kitazume , T. , Ohnogi , T. and Ito , K. 1990 . ibid , 112 : 6608
   Google Scholar
• Welch , J. T. , ed. 1991 . Selective Fluorination in Organic and Bioorganic Chemistry , Washington : American Chemical Society .
   Google Scholar
• Welch , J. T. and Eswarakrischnan , S. 1991 . Fluorine in Bioorganic Chemistry , New York : Wiley .
   Google Scholar
• Yoneda , N. 1991 . Tetrahedron , 47 : 5329
   Web of Science ®Google Scholar
• Wilkinson , J. A. 1992 . Chem. Rev. , 92 : 505
   Web of Science ®Google Scholar
• Robins , M. J. and Wnuk , S. F. 1993 . J. Org. Chem. , 58 : 3800
   Web of Science ®Google Scholar
• Xiao-Qing , T. and Chang-Ming , H. 1994 . J. Chem. Soc. Chem. Commun. , : 631
   Google Scholar
• Scherer , O. 1970 . Fortschr. Chem. Forschnung , Vol. 14/2 , Heidelberg : Springer Verlag .
   Google Scholar
• Wettstein , A. 1972 . Carbon-Fluorine Compounds: Chemistry, Biochemistry and Biological Activities , Ciba Foundation Symposium 281 Amsterdam : Associated Scientific Publishers .
   Google Scholar
• Filler , R. and Kobayashi , Y. , eds. 1982 . Biomedical Aspects of Fluorine Chemistry , Amsterdam : Elsevier .
   Google Scholar
• Sieler , M. , Jung , M. J. and Koch-Waser . 1988 . Enzyme-Activated Irreversible Inhibitors , Amsterdam : Elsevier .
   Google Scholar
• Bravo , P. and Resnati , G. 1990 . Tetrahedron Asymmetry , 1 : 661
   Web of Science ®Google Scholar
• Resnati , G. 1993 . Tetrahedron , 49 : 9385
   Web of Science ®Google Scholar
• Haddad , M. , Molines , H. and Wakselman , C. 1994 . Synthesis , : 167
   Web of Science ®Google Scholar
• Schloser , M. , Michel , D. , Guo , Z. and Shi , C. J. 1996 . Tetrahedron , 52 : 8257
   Web of Science ®Google Scholar
• Goj , O. , Kotila , S. and Haufe , G. 1996 . ibid , 52 : 12761
   Google Scholar
• Ishikawa , N. 1987 . Synthesis and Utilization of Organofluorine Compounds , Tokyo : CMC .
   Google Scholar
• Uneyama , K. 1991 . J. Synth. Org. Chem. Jpn. , 49 : 612
   Web of Science ®Google Scholar
• Banks , R. E. , Smart , B. E. and Tatlow , J. C. , eds. 1994 . Organofluorine Chemistry: Principles and Commercial Applications , New York : Plenum Press .
   Google Scholar
• For some leading references see: (a) Kirschbaum J. Analytical Profiles of Drug Substances Florey K. Academic Press NY 1983 12 1
   Google Scholar
• Shaw , K. T. , Luly , J. R. and Rapoport , H. 1985 . J. Org. Chem. , 50 : 4515
   Web of Science ®Google Scholar
• Roush , W. R. , Staub , J. A. and Brown , R. J. 1987 . J. Org. Chem. , 52 : 5127
   Web of Science ®Google Scholar
• Ojima , I. , Kato , K. , Nakahashi , K. , Fuchikami , T. and Fujita , M. 1989 . J. Org. Chem. , 54 : 4511 and references cited therein.
   Web of Science ®Google Scholar
• Manchand , P. S. , Cerruti , R. L. , Martin , J. A. , Hill , C. H. , Merrett , J. H. , Keech , E. , Belshe , R. B. , Connell , E. V. and Sim , I. S. 1990 . J. Med. Chem. , 33 : 1992
   PubMed Web of Science ®Google Scholar
• Askin , D. , Wallace , M. A. , Vacca , J. P. , Reamer , R. A. , Volante , R. P. and Shinkai , I. 1992 . J. Org. Chem. , 57 : 2771
   Web of Science ®Google Scholar
• Main , B. G. and Tucker , H. 1993 . in Medicinal Chemistry, , 2nd Ed. , Edited by: Genellin , C. R. and Roberts , S. M. 187 NY : Academic Press .
   Google Scholar
• Welch , J. T. 1987 . Tetrahedron , 43 : 3123
   Web of Science ®Google Scholar
• Barney , C. L. , Huber , E. W. and McCarthy , J. R. 1990 . Tetrahedron Lett. , 39 : 5547
   Web of Science ®Google Scholar
• Kukhar , V. P. , Svistunova , N. Y. , Soloshonok , V. A. and Solodenko , V. A. 1993 . Russ. Chem. Rev. Engl. , 62 : 284
   Google Scholar
• Soloshonok , V. A. , Kirilenko , A. G. , Kukhar , V. P. and Resnati , G. 1993 . Tetrahedron Lett. , 34 : 3621
   Web of Science ®Google Scholar
• Kukhar , V. P. and Soloshonok , V. A. , eds. 1994 . Fluorine Containing Amino Acids: Synthesis and Properties , NY : Wiley .
   Google Scholar
• Soloshonok , V. A. , Kirilenko , A. G. , Kukhar , V. P. and Resnati , G. 1994 . Tetrahedron Lett. , 35 : 3119
   Web of Science ®Google Scholar
• Soloshonok , V. A. and Kukhar , V. P. 1996 . Tetrahedron , 52 : 6953
   Web of Science ®Google Scholar
• Soloshonok , V. A. and Ono , T. 1996 . ibid , 52 : 14701
   Google Scholar
• Ono , T. , Kukhar , V. P. and Soloshonok , V. A. 1996 . J. Org. Chem. , 61 : 6563
   PubMed Web of Science ®Google Scholar
• For reviews on reductive aminations see: (a) Emerson W. S. Organic Reactions Wiley New York 1948 4 174
   Google Scholar
• Lane , C. F. 1975 . Synthesis , : 135
   Web of Science ®Google Scholar
• Hutchins , R. O. and Natale , N. 1979 . Org. Prep. Proced. Int. , 11 : 201
   Web of Science ®Google Scholar
• Whitesell , J. K. 1991 . Comprehensive Organic Synthesis , Edited by: Trost , B. M. and Fleming , I. Vol. 6 , 724 Oxford : Pergamon Press . and Vol. 8 p. 25.
   Google Scholar
• Gribble , G. W. 1996 . Reductions in Organic Synthesis, ACS Symposium Series 641 , Edited by: Abdel-Majid , A. F. 167 Washington , DC : American Chemical Society .
   Google Scholar
• Abdel-Majid , A. F. ibid , 201
   Google Scholar
• Borch , R. F. , Bernstein , M. D. and Durst , H. D. 1971 . J. Am. Chem. Soc. , 93 : 2897
   Web of Science ®Google Scholar
• Borch , R. F. 1988 . Org. Synth. Coll. , Vol. 6 : 499
   Google Scholar
• Lenga , R. E. , ed. 1985 . The Sigma-Aldrich Library of Chemical Safety Data, , Ist Edition , 1609 Sigma-Aldrich Corp. .
   Google Scholar
• Moorman , A. E. 1993 . Synth. Commun , 23 : 789
   Web of Science ®Google Scholar
• Gribble , G. W. , Lord , P. D. , Skotnicki , J. , Dietz , S. E. , Eaton , J. T. and Johnson , J. L. 1974 . J. Am. Chem. Soc. , 96 : 7812
   Web of Science ®Google Scholar
• Gribble , G. W. , Jasinski , J. M. , Pellicone , J. T. and Panetta , J. A. 1978 . Synthesis , : 766
   Web of Science ®Google Scholar
• Abdel-Majid , A. F. , Maryanoff , C. A. and Carson , K. G. 1990 . Tetrahedron Lett. , 31 : 5595
   Web of Science ®Google Scholar
• Abdel-Magid , A. F. and Maryanoff , C. A. 1990 . Synlett , : 537
   Web of Science ®Google Scholar
• Abdel-Majid , A. F. , Carson , K. G. , Harris , B. D. , Maryanoff , C. A. and Shah , R. D. 1996 . J. Org. Chem. , 61 : 3849
   PubMed Web of Science ®Google Scholar
• Verado , G. , Giumanini , A. G. , Strazzolini , P. and Poina , M. 1993 . Synthesis , : 121
   Web of Science ®Google Scholar
• Pelter , A. , Rosser , R. M. and Mills , S. 1983 . Ventron Alembic , : 30
   Google Scholar
• Bomann , M. D. , Guch , I. C. and Di Mare , M. 1995 . J. Org. Chem. , 60 : 5995
   Web of Science ®Google Scholar
• Bhattacharyya , S. 1994 . Tetrahedron Lett. , 35 : 2401
   Web of Science ®Google Scholar
• Bhattacharyya , S. 1994 . Synlett , : 1029
   Web of Science ®Google Scholar
• Bhattacharyya , S. 1995 . J. Org. Chem. , 60 : 4928
   Web of Science ®Google Scholar
• Bhattacharyya , S. 1995 . Synlett , : 971
   Web of Science ®Google Scholar
• Bhattacharyya , S. , Chatterjee , A. and Williamson , J. S. 1995 . Synlett , : 1079
   Web of Science ®Google Scholar
• Bhattacharyya , S. 1996 . Organometallics , 15 : 1065
   Web of Science ®Google Scholar
• Bhattacharyya , S. 1996 . J. Chem. Soc. Perkin Trans 1 , : 1381
   Google Scholar
• Bhattacharyya , S. , Chatterjee , A. and Duttachoudhury , S. K. 1994 . J. Chem. Soc. Perkin Trans 1 , : 1
   Google Scholar
• Ranu , B. C. 1993 . Synlett. , : 885 and references cited therein.
   Web of Science ®Google Scholar
• Grabbe , P. , Garcia , G. A. and Rius , C. 1973 . J. Chem. Soc. Perkin Trans 1 , : 810
   Google Scholar