Alkylation of aromatic amines and related compounds using a copper(II)-aluminum(III) couple

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3295-3298

  Barton, Derek H R ^a   Doris, Eric ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ALKYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029916140     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00579-5     Document Type: Article

References (13)

1. For a review on organoaluminum chemistry, see: Mole, T.; Jeffery, E. A. Organoaluminum compounds, Elsevier: New York, 1972. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001-5032.
2. For a review on organoaluminum chemistry, see: Mole, T.; Jeffery, E. A. Organoaluminum compounds, Elsevier: New York, 1972. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001-5032.
3. Eisch, J. J. in Comprehensive Organometallic Chemistry, Vol. 1, G. Wilkinson, F. G. A. Stone and E. W. Abel Eds., Pergamon Press: Oxford, 1982.
4. Ziegler, K.; Holzkamp, H.; Breil, H.; Martin, H. Angew. Chem. 1955, 67, 541-547. Natta, G. Angew. Chem. 1956, 68, 393-403.
5. Ziegler, K.; Holzkamp, H.; Breil, H.; Martin, H. Angew. Chem. 1955, 67, 541-547. Natta, G. Angew. Chem. 1956, 68, 393-403.
6. Barton, D. H. R.; Finet, J. P. Pure Appl. Chem. 1987, 59, 937-946. Abramovitch, R. A.; Barton, D. H. R.; Finet, J. P. Tetrahedron, 1988, 44, 3039-3071. Barton D. H. R. Heteroatom Chemistry, E. Block Ed., VCH Inc.: New York, 1990.
7. Barton, D. H. R.; Finet, J. P. Pure Appl. Chem. 1987, 59, 937-946. Abramovitch, R. A.; Barton, D. H. R.; Finet, J. P. Tetrahedron, 1988, 44, 3039-3071. Barton D. H. R. Heteroatom Chemistry, E. Block Ed., VCH Inc.: New York, 1990.
8. Barton, D. H. R.; Finet, J. P. Pure Appl. Chem. 1987, 59, 937-946. Abramovitch, R. A.; Barton, D. H. R.; Finet, J. P. Tetrahedron, 1988, 44, 3039-3071. Barton D. H. R. Heteroatom Chemistry, E. Block Ed., VCH Inc.: New York, 1990.
9. 2O. The residue was redissolved in THF and filtered over paper. After evaporation of the solvent, the hydrated copper pivalate was dried overnight under reduced pressure at 80-85°C.
10. Westermann, J.; Nickisch, K. Angew. Chem. Int. Ed. 1993, 52, 1368-1370.
11. A referee suggested that the reaction might proceed through reductive elimination of an Amine-Cu-Et complex.
12. 2 as carrier gas. The chromatography column is a D-B 5 (30 m × 0.322 mm × 0.25 μm).
13. +: 179.1184, Found: 179.1191.