Ruthenium-Catalyzed C-H Bond Heteroarylation of Triazoles Enabled by a Deconvolution Strategy - Université de Rennes Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2018

Ruthenium-Catalyzed C-H Bond Heteroarylation of Triazoles Enabled by a Deconvolution Strategy

Abstract

Reaction optimization for C–H bond functionalization reactions with transition‐metal catalysts is traditionally based on long and tedious screening of multiple conditions. In this contribution we have applied a deconvolution strategy to identify reaction conditions suitable for the C–H bond heteroarylation of 1,2,3‐triazoles with a ruthenium catalyst by performing only 18 experiments with mixtures of reagents instead of the theoretically 576 experiments that should have been considered individually. The activation and functionalization takes place at the ortho position of the phenyl ring attached to the 1,2,3‐triazole directing group as confirmed by X‐ray crystallographic studies. The bis‐ vs. mono‐heteroarylation was controlled by tuning the stoichiometry of the reagents. Such methodology was also applicable to aryl bromide coupling partners bearing ortho and meta substituents.
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hal-01897465 , version 1 (08-11-2018)

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Rafael Gramage-Doria, Thierry Roisnel. Ruthenium-Catalyzed C-H Bond Heteroarylation of Triazoles Enabled by a Deconvolution Strategy. European Journal of Organic Chemistry, 2018, 2018 (44), pp.6083-6087. ⟨10.1002/ejoc.201800843⟩. ⟨hal-01897465⟩
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