Journal
TETRAHEDRON
Volume 61, Issue 52, Pages 12238-12243Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.09.111
Keywords
N-tosyl imines; diethylzinc; reduction; ethylation; solvent effect; coordination
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The effect of coordination on the reaction of N-tosyl imines and diethylzinc was studied in detail. It showed that there was strong coordination between N-tosyl imine and diethylzinc. Due to this coordination, N-tosyl imines could be reduced directly through the P-H transferring mechanism by diethylzinc in nonpolar solvents to afford the corresponding secondary amines in excellent yields at mild conditions. The coordination of diethylzinc and N-tosyl imine was hindered by reacting in polar solvents or adding TMEDA to the reaction, it afforded ethylating product partially or exclusively. (c) 2005 Elsevier Ltd. All rights reserved.
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