Towards a sustainable synthesis of amides: chemoselective palladium-catalysed aminocarbonylation of aryl iodides in deep eutectic solvents

Author(s): Francesco Messa ¹ ^, ² ^, ³ ^, ⁴ , Serena Perrone ¹ ^, ² ^, ³ ^, ⁴ , Martina Capua ¹ ^, ² ^, ³ ^, ⁴ , Francesco Tolomeo ¹ ^, ² ^, ³ ^, ⁴ , Luigino Troisi ¹ ^, ² ^, ³ ^, ⁴ , Vito Capriati ⁵ ^, ⁶ ^, ⁷ ^, ⁸ ^, ⁴ , Antonio Salomone ¹ ^, ² ^, ³ ^, ⁴

Publication date (Electronic): 2018

Journal: Chemical Communications

Publisher: Royal Society of Chemistry (RSC)

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Abstract

A Pd-catalysed aminocarbonylation of aryl iodides has been first achieved in environmentally responsible and recyclable deep eutectic solvents.

Abstract

A palladium-catalysed aminocarbonylation of (hetero)aryl iodides has, for the first time, been accomplished in deep eutectic solvents as environmentally benign and recyclable media, under mild conditions. The reactions proceeded with a good substrate scope, and a variety of amides have been synthesized in yields up to 98%.

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The atom economy--a search for synthetic efficiency.

B. Trost (1991)

Efficient synthetic methods required to assemble complex molecular arrays include reactions that are both selective (chemo-, regio-, diastereo-, and enantio-) and economical in atom count (maximum number of atoms of reactants appearing in the products). Methods that involve simply combining two or more building blocks with any other reactant needed only catalytically constitute the highest degree of atom economy. Transition metal-catalyzed methods that are both selective and economical for formation of cyclic structures, of great interest for biological purposes, represent an important starting point for this long-term goal. The limited availability of raw materials, combined with environmental concerns, require the highlighting of these goals.