Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments

Abstract

Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM) cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the direct SM acylative coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis.

Mastering tricyclic ring systems for desirable functional cannabinoid activity

“…The preparation of amines 28 and 30 was achieved by palladium-catalyzed coupling in analogy to known literature methods (e.g. [21]).…”

Catalytic C−H/C−F Coupling of Azoles and Acyl Fluorides

“…Transition‐metal‐catalyzed cross‐coupling reactions of acyl electrophiles with aryl nucleophiles represent a powerful and reliable synthetic strategy for the introduction of acyl fragments into aromatic rings to provide aromatic ketones, and a large variety of carboxylic acid derivatives are currently used as acyl electrophiles . Among these, acyl fluorides have recently gained much attention as valuable carbon‐based electrophiles in cross‐coupling reactions, especially in acyl coupling and decarbonylative coupling reactions .…”

“…Among these, acyl fluorides have recently gained much attention as valuable carbon‐based electrophiles in cross‐coupling reactions, especially in acyl coupling and decarbonylative coupling reactions . Due to the moderate electrophilicity of acyl fluorides, they exhibit a good balance between stability and reactivity with respect to their compatibility under nucleophilic conditions, that is, they are more stable than the commonly employed acyl chlorides, yet more reactive than the corresponding esters and amides . In fact, acyl fluorides are isolable using column chromatography on silica gel and can be used without any special precautions against moisture.…”

Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

“…This reaction has found several applications in organic synthesis due to its versatility, high stability and low toxicity of the required starting materials which mostly commercially available or readily accessible. In addition, the introduction of various substrates of organoborane reagents is practically simple and the resultants often remain unaffected throughout subsequent transformations in the presence of immensely functionalized biomolecules, molecular oxygen, water and can frequently be performed under ambient reaction conditions …”