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/PMC8018292 | PMC |
http://dx.doi.org/10.1021/acssuschemeng.0c05049 | DOI Listing |
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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