Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions

Alexey Volkov, Fredrik Tinnis and Hans Adolfsson*

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

A. Volkov, F. Tinnis, H. Adolfsson, Org. Lett., 2014, 16, 680-683.

DOI: 10.1021/ol403302g

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Abstract

A transition-metal-free catalytic hydrosilylation based on t-BuOK (5 mol %) and (MeO)₃SiH or (EtO)₃SiH allows the reduction of tertiary amides to their corresponding enamines with high selectivity in very good yields.

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Key Words

Enamines, Deoxygenation, Silanes

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ID: J54-Y2014