Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(I) bis-metal sequential catalysis

Pei-Qiang Huang; Wei Ou; Feng Han

doi:10.1039/C6CC05318A

Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(i) bis-metal sequential catalysis†

Pei-Qiang Huang,

*^ab Wei Ou^a and Feng Han^a

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* Corresponding authors

^a Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China
E-mail: pqhuang@xmu.edu.cn

^b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China

Abstract

We report herein a convenient and versatile method for the direct reductive alkynylation of tertiary amides to give propargylic amines through sequential Ir-catalysed hydrosilylation–Cu(I)-catalysed alkynylation. The reactions proceed chemoselectively at the amide group in the presence of several sensitive functional groups including the very reactive aldehyde group on either the amide or the alkyne coupling partner. The method is general for tert-amides with or without α-hydrogen.

This article is part of the themed collection: Celebrating a Century of Excellency in Chemistry at Xiamen University

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DOI: https://doi.org/10.1039/C6CC05318A
Article type: Communication
Submitted: 26 6 2016
Accepted: 30 8 2016
First published: 05 9 2016
This article is Open Access

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Chem. Commun., 2016,52, 11967-11970

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Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(I) bis-metal sequential catalysis

P. Huang, W. Ou and F. Han, Chem. Commun., 2016, 52, 11967 DOI: 10.1039/C6CC05318A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Communications

Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(i) bis-metal sequential catalysis†

Abstract

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Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(I) bis-metal sequential catalysis

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