Abstract
Palladium-catalyzed carbonylation reaction has surfaced as a robust tool for insertion of the carbonyl group into organic molecules, and in the last decades enormous progress has been made. Nowadays, a plethora of methodologies is available to synthesize all kinds of carbonyl compounds. However, the focus has shifted during recent years to address rising concerns related to developing safe, cost-efficient, and more sustainable methodologies. The use of different carbon monoxide (CO) precursors/sources, avoiding handling of highly toxic and flammable gaseous carbon monoxide, and substituting nonrenewable solvents for those derived from renewable feedstock have contributed to aim these goals. In this review, we will discuss the advent of the application of renewable solvents to improve the sustainability and environmentally benign nature of Pd-catalyzed carbonylation reactions.
Highlights
Growing concern over the impact of chemical processes, associated with the rising price of oil, as well as, the need to search for greener, sustainable, and economically viable chemicals, has prompted the scientific community around the world to develop new cost-efficient, environmentally benign and efficient synthetic protocols to minimize waste generation and attend the demand for chemical products from an ever-increasing population.[1,2,3,4,5] Solvents are present in most chemical processes and generally account for the primary source of the wasted mass of fine chemical and pharmaceutical industry
Our group[67] proposed the use of dimethyl carbonate (DMC) as a high biodegradability ecofriendly and low toxicity solvent. Employing this solvent in combination with a sealed two chamber reactor (COware) we developed a sustainable synthesis of 1,4,5-trisubstituted 1,2,3-triazole-5-carboxamides starting from 1,4-disubstituted-5‐iodo-1,2,3-triazoles and accessible alkyl amines employing formic acid as an efficient, low-cost, and readily available carbon monoxide precursor (Scheme 9)
Palladium-catalyzed carbonylation reactions have emerged as robust and versatile synthetic tools to access a wide variety of carbonyl compounds
Summary
Growing concern over the impact of chemical processes, associated with the rising price of oil, as well as, the need to search for greener, sustainable, and economically viable chemicals, has prompted the scientific community around the world to develop new cost-efficient, environmentally benign and efficient synthetic protocols to minimize waste generation and attend the demand for chemical products from an ever-increasing population.[1,2,3,4,5] Solvents are present in most chemical processes and generally account for the primary source of the wasted mass of fine chemical and pharmaceutical industry. The challenge associated with this strategy is the requirement for handling large volumes of gaseous, corrosive, odorless and highly toxic CO from a pressurized cylinder (Scheme 1a) Extensive research on this field led to the advent of CO-releasing molecules (CORMs) for generating CO gas in and ex situ during the reaction (Scheme 1a).[51,55,66] In such a way, different methodologies based on Pd-catalyzed carbonylation reactions have been reported[67,68,69,70,71,72,73,74,75,76,77,78] to prepare highly valuable compounds, such as aldehydes, ketones, carboxylic acids, and their derivatives. The carbonylation reactions that do not fit in any of these solvents or that fit in more than one is compiled in the Miscellaneous sub-section
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