Carbon monoxide surrogates for palladium-catalyzed Suzuki-Miyaura and Sonogashira carbonylative cross-coupling reactions

Abstract

Palladium-catalyzed Suzuki-Miyaura and Sonogashira reactions are probably the best methods to create new sp2-sp2 and sp2-sp chemical bonds starting from aryl halides and aryl boronic acids or terminal alkynes. These cross-couplings are generally promoted by a palladium-based catalyst and due to their potentialities, they have been deeply investigated. In particular, the carbonylative version of this reactions is widely used for the synthesis of conjugated diaryl and alkynyl ketones, biologically active compounds, and important building blocks for the synthesis of pharmaceuticals, and organic materials. The insertion of a carbon monoxide molecule is generally achieved by means of high pressure of CO but nowadays the severe toxicity of this gas has led to the development of CO surrogates which must be non-toxic and easy to handle. In this context, the aim of this review is to give a detailed comprehensive overview of the scientific literature regarding carbonylative Suzuki-Miyaura and Sonogashira reactions performed employing a CO source. The content of this review will be divided into two main chapters according to the different approach to CO generation, i.e., -in situ and ex situ technique. For each chapter, a systematic analysis of the nature of the CO surrogate will be reported.