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

Org. Lett., 2014, 16 (3), pp 680–683

DOI: 10.1021/ol403302g

Publication Date (Web): January 22, 2014

Abstract

Tertiary amides are efficiently reduced to their corresponding enamines under hydrosilylation conditions, using a transition-metal-free catalytic protocol based on t-BuOK (5 mol %) and (MeO)₃SiH or (EtO)₃SiH as the reducing agent. The enamines were formed with high selectivity in good-to-excellent yields.

Supporting Information

Experimental procedures and spectroscopic data. This material is available free of charge via the Internet at http://pubs.acs.org.

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Letter

Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions

Abstract

Supporting Information

PDF

Transformation of Amides into Highly Functionalized Triazolines

An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides

Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines

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Syntheses of Sterically Bulky Schiff-Base Magnesium Complexes and Their Application in the Hydrosilylation of Ketones

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Palladium on Carbon-Catalyzed Silane-Reduction of Tertiary Carboxamides: Soluble Palladium Colloids are an Active Catalyst Species

Potassium Hydroxide-Catalyzed Chemoselective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of ω-Hydroxylactams and Lactams

Potassium Phosphate-Catalyzed Chemoselective Reduction of α-Keto Amides: Route to Synthesize Passerini Adducts and 3-Phenyloxindoles

An efficient and green approach to synthesizing enamines by intermolecular hydroamination of activated alkynes

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Phosphazenes: efficient organocatalysts for the catalytic hydrosilylation of carbon dioxide

Direct transformation of amides: a one-pot reductive Ugi-type three-component reaction of secondary amides

Efficient and Selective Synthesis of E -Vinylamines via Tungsten(0)-Catalyzed Hydroamination of Terminal Alkynes

Cesium Carbonate Catalyzed Chemoselective Hydrosilylation of Aldehydes and Ketones under Solvent-Free Conditions

ChemInform Abstract: Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions.

Efficient metal-free hydrosilylation of tertiary, secondary and primary amides to amines

Mo(CO) 6 catalysed chemoselective hydrosilylation of α,β-unsaturated amides for the formation of allylamines

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Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions

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