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Synfacts 2018; 14(09): 0987
DOI: 10.1055/s-0037-1610614
DOI: 10.1055/s-0037-1610614
Polymer-Supported Synthesis
Palladium/Carbon-Catalyzed Flow C–H Functionalization of 1,2,3-Triazoles
Ferlin F.
Luciani L.
Santoro S.
Marrocchi A.
Lanari D.
Bechtoldt A.
Ackermann L.
Vaccaro L.
* Università di Perugia, Italy and Georg-August-Universität Göttingen, Germany
A Continuous Flow Approach for the C–H Functionalization of 1,2,3-Triazoles in γ-Valerolactone as a Biomass-Derived Medium.
Green Chem. 2018;
20: 2888-2893
A Continuous Flow Approach for the C–H Functionalization of 1,2,3-Triazoles in γ-Valerolactone as a Biomass-Derived Medium.
Green Chem. 2018;
20: 2888-2893
Further Information
Publication History
Publication Date:
20 August 2018 (online)
Key words
palladium catalysis - C–H functionalization - cyclization - triazoles - valerolactone - continuous-flow reaction
Significance
A continuous-flow C–H functionalization and cyclization of 1,2,3-triazoles bearing haloaryl groups was carried out by using a coil reactor containing palladium on carbon catalyst (Pd/C) in γ-valerolactone (GVL), as a biomass-derived reaction medium, to give the corresponding cyclic compounds (eq. 1: ≤91% yield; eq. 2: ≤93% yield).
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Comment
A long-term reaction of 4-[(2-iodophenoxy)methyl]-1-(4-methoxyphenyl)-1H-1,2,3-triazole in a coil reactor containing Pd/C for eight hours gave 24 g of the cyclized product (87% yield). MP-AES analysis of the reaction mixture showed that 0.0015% of the palladium species leached out during this long-term reaction.
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