Condensation Versus Hydroamination for the Direct, Catalytic Synthesis of Tetrasubstituted Propargylamines

Keegan G. Nelson; Catharine H. Larsen

doi:10.1055/s-0034-1379246

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(19): 2681-2685
DOI: 10.1055/s-0034-1379246

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Condensation Versus Hydroamination for the Direct, Catalytic Synthesis of Tetrasubstituted Propargylamines

Keegan G. Nelson

Department of Chemistry, University of California, Riverside, 501 W. Big Springs Road, Riverside, CA 92521, USA Fax: +1(951)827-4713 eMail: catharine.larsen@ucr.edu

,

Catharine H. Larsen*

Department of Chemistry, University of California, Riverside, 501 W. Big Springs Road, Riverside, CA 92521, USA Fax: +1(951)827-4713 eMail: catharine.larsen@ucr.edu

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Abstract

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Abstract

Multicomponent couplings of carbonyls, amines, and nucleophiles provide a wide array of trisubstituted carbons bearing amines but tetrasubstituted products are rarely formed. Cooperative copper/titanium catalysis under solvent-free conditions is required to overcome the barrier to condensation of a ketone with an amine and subsequent alkynylation. An alternative mode of accessing ketimines is the Markovnikov hydroamination of alkynes. Heating a simple copper salt with an amine and a terminal alkyne rapidly produces tetrasubstituted propargylic amines via tandem hydroamination–alkynylation.

Key words

green chemistry - catalysis - tandem reaction - ketones - amines - alkynes

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Referenzen

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