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Ruthenium‐Catalyzed C–H Bond Heteroarylation of Triazoles Enabled by a Deconvolution Strategy
Author(s) -
GramageDoria Rafael,
Roisnel Thierry
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800843
Subject(s) - chemistry , ruthenium , reagent , catalysis , combinatorial chemistry , surface modification , bromide , stoichiometry , aryl , ring (chemistry) , organic chemistry , alkyl
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.