H2-Mediated Copper Catalyzed C–C Coupling Reactions – Selective Formation of Skipped Dienes

13 April 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A simple copper(I)/N-heterocyclic carbene complex facilitates a H2-mediated C–C coupling reaction of internal alkynes and allylic chlorides. The catalytic protocol delivers the corresponding 1,4-dienes (skipped dienes) with high chemo-, regio- and stereoselectivity without any isomerization to the thermodynamically more stable 1,3-dienes or overreduction to the corre-sponding alkanes. The H2-mediated C–C coupling reaction allows for the exploitation “copper hydride catalysis” with H2 as terminal reducing agent and source of hydrides for forging of new C–C bonds. In this way, this approach gives rise to C–C bond forming reactions with a 3d metal without the need for a stoichiometric organometallic reducing agent.

Keywords

copper
hydrogen
alkynes
NHC ligands
allylic substitution

Supplementary materials

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Description
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Supporting Information
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practical procedures and spectral characterization of all starting materials and catalysis products
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Supporting Information - Spectra Catalysis Products
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contains spectra of all catalysis products
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Supporting Information - Spectra Starting Materials
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contains spectra of all starting materials
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