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Mild and Selective Et2Zn-Catalyzed Reduction of Tertiary Amides under Hydrosilylation Conditions

Oleksandr O. Kovalenko, Alexey Volkov and Hans Adolfsson*

*Department of Organic Chemistry, Arrhenius Laboratory Stockholm University, SE-106 91, Stockholm, Sweden, Email: hansaorgan.su.se

O. O. Kovalenko, A. Volkov, H. Adolfsson, Org. Lett., 2015, 17, 446-449.

DOI: 10.1021/ol503430t (free Supporting Information)


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Abstract

Diethylzinc (Et2Zn) is an efficient and chemoselective catalyst for the reduction of tertiary amides under mild reaction conditions employing polymeric silane (PMHS) as a cost-effective hydride source. Crucial for the catalytic activity was the addition of a substoichiometric amount of lithium chloride. A series of amides containing different additional functional groups were reduced to their corresponding amines in very good yields.

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Key Words

reduction of amides, PMHS


ID: J54-Y2015