Regioselective Ru(II)/Pd(0) Dual Catalysis: One-Pot C–H Diarylation of Five-Membered Heterocyclic Derivatives

Herein, we report a one-pot site-selective dual metal catalyzed C–H diarylation reaction for the synthesis of multiarylated thiophene and furan derivatives in yields up to 92%. The regioselectivity of the developed methodology was achieved with the sequential use of two metal catalysts within a sing...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 4; pp. 3138 - 3151
Main Authors Al Mamari, Hamad H, Grošelj, Uroš, Požgan, Franc, Brodnik, Helena
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.02.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
DIRECT ARYLATION
RU
DIASTEREOSELECTIVE SYNTHESIS
PD
HETEROARYLATION
BOND ACTIVATION
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Summary:Herein, we report a one-pot site-selective dual metal catalyzed C–H diarylation reaction for the synthesis of multiarylated thiophene and furan derivatives in yields up to 92%. The regioselectivity of the developed methodology was achieved with the sequential use of two metal catalysts within a single vessel, starting with a Ru­(II)-catalyzed C3 arylation assisted by an azine directing group, followed by a Pd(0)-catalyzed C–H functionalization on the C5-position of the five-membered heterocycle. Furthermore, the kinetic studies support that the position of the nitrogen atom within the azine moiety exhibits an evident effect on the efficiency of the ruthenium-catalyzed arylation step.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.0c01983