Abstract
Solvents constitute the largest component for many chemical processes and substitution of nonrenewable solvents is a longstanding goal for green chemistry. Here, we show that Pd-catalyzed carbonyla...
Highlights
According to the development plan of the United Nations General Assembly “Transforming Our World: The 2030 Agenda for Sustainable Development” initiated in 2015, considerable efforts are needed over the coming decade to build a better and more sustainable future.[1]
A range of renewable solvents were studied for carbonylative couplings of aryl bromides with arylboronic acids,[12] amines,[13] and alcohols (Figure 1).[14]
We decided to focus on Pd-based catalytic systems that have proven to be versatile catalysts for carbonylative couplings.11k,12−14 For safety reasons, the reactions were conducted in two chamber reactors (COware) developed in the group of Skrydstrup using stoichiometric quantities of CO generated ex situ from COgen (9-methyl-9Hfluorene-9-carbonyl chloride).10e The solvent’s polarity was approximated as nonpolar and polar based on their dielectric constant; a solvent was classified as polar if the dielectric constant was over 5 (Figure 1, Table S1)
Summary
According to the development plan of the United Nations General Assembly “Transforming Our World: The 2030 Agenda for Sustainable Development” initiated in 2015, considerable efforts are needed over the coming decade to build a better and more sustainable future.[1]. Most of the industrial processes and the pharmaceutical industry are largely based on the application of nonrenewable solvents, which usually constitute over 80% of materials needed for the production of the final ingredients.[2] As a result, yearly manufacture of nonrenewable and hazardous common organic solvents exceeds 20 million metric tons.2d A recent survey on the solvents used in the pharmaceutical industry for the period 1997−2012 revealed that the top 10 most frequently used solvents are dichloromethane, hexane, diisopropyl ether, 1,2-dimethoxyethane, 1,4-dioxane, 1,2dichloroethane, diethyl ether, chloroform, diglyme, and chlorobenzene.[3] This unsustainable practice can be addressed by the development and popularization of renewable and safe solvent candidates. The most frequently used solvents available from biomass are polar protic ethanol, glycerol and its derivatives, and choline chloride-based deep eutectic solvents, polar aprotic 2methyltetrahydrofuran (2MeTHF), cyrene and γ-valerolactone (GVL), as well as nonpolar limonene and p-cymene
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