Статья

Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend

Tommaso FantoniDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalySara BernardoniDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalyAlexia MattelloneDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalyGiulia MartelliDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalyLucia FerrazzanoDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalyPaolo CantelmiDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalyDario CorbisieroDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalyAlessandra TolomelliDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalyWalter CabriDepartment of Chemistry Giacomo Ciamician Alma Mater Studiorum University of Bologna Via Selmi 2 40136 Bologna ItalyFederica VacondioDepartment of Food and Drug Sciences University of Parma Parco Area delle Scienze 27/a 43124- Parma ItalyFrancesca FerlenghiDepartment of Food and Drug Sciences University of Parma Parco Area delle Scienze 27/a 43124- Parma ItalyMarco MorDepartment of Food and Drug Sciences University of Parma Parco Area delle Scienze 27/a 43124- Parma ItalyAntônio RicciInnovation and Development Fresenius kabi iPsum via San Leonardo 23 45010 Villadose (RO) Italy

2021en

ABI

Аннотация

Abstract The identification of a green, versatile, user‐friendly, and efficient methodology is necessary to facilitate the use of Heck‐Cassar‐Sonogashira (HCS) cross‐coupling reaction in drug discovery and industrial production in the pharmaceutical segment. The Heck‐Cassar and Sonogashira protocols, using N ‐hydroxyethylpyrrolidone (HEP)/water/ N,N,N′,N′ ‐tetramethyl guanidine (TMG) as green solvent/base mixture and sulfonated phosphine ligands, allowed to recycle the catalyst, always guaranteeing high yields and fast conversion under mild conditions, with aryl iodides, bromides, and triflates. No catalyst leakage or metal contamination of the final product were observed during the HCS recycling. To our knowledge, a turnover number (TON) up to 2375, a turnover frequency (TOF) of 158 h −1 , and a process mass intensity (PMI) around 7 that decreased around 3 after solvent, base, and palladium recovery, represent one of the best results to date using a sustainable protocol. The Heck‐Cassar protocol using sSPhos was successfully applied to the telescoped synthesis of Erlotinib (TON: 1380; TOF: 46 h −1 ).

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Идентификаторы

DOI: 10.1002/cssc.202100623

Цитирования и источники

Цитирований: 2Использованных источников: 0

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