Recent Advances in Transition-Metal-Catalyzed Sonogashira Cross-Coupling Reactions of Alkyl Electrophiles

Abstract Catalytic Sonogashira cross-coupling reactions represent an efficient and versatile approach for constructing complex alkynes from readily available starting materials. Despite notable progress in this field, the development of transition-metal-catalyzed Sonogashira cross-coupling reactions of alkyl electrophiles remains limited. This limitation primarily stems from the low reactivity and pronounced propensity of these compounds towards β-H elimination. To overcome these challenges, researchers have investigated the use of palladium, nickel, and copper catalysts for Sonogashira reactions of alkyl electrophiles. Furthermore, significant strides have been made in achieving asymmetric Sonogashira cross-coupling reactions of electrophiles. This short review provides an overview of recent breakthroughs in this area. 1 Introduction 2 Palladium-Catalyzed Sonogashira Cross-Coupling of Alkyl Halides 3 Nickel-Catalyzed Sonogashira Cross-Coupling of Alkyl Halides 4 Copper-Catalyzed Sonogashira Cross-Coupling of Alkyl Electrophiles 4.1 Copper-Catalyzed Racemic Sonogashira Cross-Coupling of Alkyl Electrophiles 4.2 Copper-catalyzed Asymmetric Sonogashira Cross-Coupling of Alkyl Electrophiles 5 Conclusions and Perspectives