Carbon monoxide (CO) has become one of the most relevant and versatile renewable C1 building blocks for chemical synthesis, especially in the fine chemicals industry, due to the development of efficient and selective catalysts for its activation. In this review, we present a comprehensive critical analysis of the last 10 years literature on the use of CO as a renewable feedstock for fine chemicals production. The review is organized by type of catalytic reaction, namely alkene and alkyne carbonylation, hydroformylation, carbonylation of aryl halides, carbonylative cross‐coupling and C–H carbonylation. Notable examples of the synthesis of relevant building blocks and/or known pharmaceuticals are highlighted. Emphasis is placed on examples of utilizing CO as the C1 building block in one or more catalytic steps. The catalyst used and the reaction conditions are consistently presented throughout all of the examples.This article is protected by copyright. All rights reserved.

Carbon monoxide as a C1 building block in fine chemical synthesis

Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis of simple building blocks as well as for the functionalization of biologically important skeletons. This review covers the history of carbonylative coupling reactions in Hungary between the years 1994 and 2021.

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27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

Herein we describe an efficient continuous flow process that integrates a custom-designed gas input control system, coupled with a tubular reactor for Pd-catalyzed aminocarbonylation for producing carboxamides in multigram scale,... 

Gas-Liquid Tubular Continuous-Flow Pd-catalyzed Aminocarbonylation Process for Scalable Synthesis of Carboxamides

Palladium-catalyzed aminocarbonylation of heteroaryl iodides is reported in the presence of chloroform as the carbon monoxide surrogate. The substrate scope of the reaction was demonstrated by the synthesis of quinoline-3-carboxamides and other heteroaryl amides in yields up to 90 % under non-inert conditions and microwave irradiation at 80 °C in 30 min. This carbonylation method provides efficient access to previously inaccessible biologically important heteroaryl carboxamides. 

Palladium‐Catalyzed Aminocarbonylation of Heteroaryl Iodides

In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different conditions, such as temperatures, pressures, and ligands. It was shown that the XantPhos ligand had a great influence on conversion (98%) and chemoselectivity (100% carboxamide), compared with the monodentate PPh3. Following this study, the optimized conditions were used to extend the scope of substrates with nineteen candidates (various para-, ortho-, and meta-substituted iodobenzene derivatives and iodo-heteroarenes), as well as eight different amine nucleophiles.

https://www.mdpi.com/1420-3049/28/1/442/pdf?version=1672988560

Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance.

https://www.mdpi.com/1420-3049/26/6/1813/pdf

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation.

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Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation.