Polarclean/Water as a Safe and Recoverable Medium for Selective C2-Arylation of Indoles Catalyzed by Pd/C.

ACS Sustain Chem Eng

Laboratory of Green S.O.C. - Dipartimento di Chimica, biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia - I, Italy.

Published: November 2020

Herein, we report the use of nontoxic, water-miscible Polarclean as a safe dipolar aprotic solvent for the metal-catalyzed direct C2-H arylation of indoles using Pd/C as a catalyst. The developed method allows reaching excellent yields and regioselectivities, and it tolerates various substituents on both indole and diaryliodonium salt scaffolds. Polarclean is fully recoverable and reusable; it shows a very low leaching of the metal catalyst, allowing its complete recovery and reuse for at least six representative reaction runs.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8018292PMC
http://dx.doi.org/10.1021/acssuschemeng.0c05049DOI Listing

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Polarclean/Water as a Safe and Recoverable Medium for Selective C2-Arylation of Indoles Catalyzed by Pd/C.

ACS Sustain Chem Eng

November 2020

Laboratory of Green S.O.C. - Dipartimento di Chimica, biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia - I, Italy.

Herein, we report the use of nontoxic, water-miscible Polarclean as a safe dipolar aprotic solvent for the metal-catalyzed direct C2-H arylation of indoles using Pd/C as a catalyst. The developed method allows reaching excellent yields and regioselectivities, and it tolerates various substituents on both indole and diaryliodonium salt scaffolds. Polarclean is fully recoverable and reusable; it shows a very low leaching of the metal catalyst, allowing its complete recovery and reuse for at least six representative reaction runs.

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