DOI: https://doi.org/10.55373/mjchem.v25i2.127

Keywords: Stille reaction; palladium; copper; nickel; catalyst; optimization

Abstract

Stille reaction is one of the most common, efficient and selective Pd-catalyzed cross-coupling reactions for the construction of C-C bonds in organic synthesis. It was initially achieved and reported in 1978 by J. K. Stille and D. Milstein. This reaction is based on organotin compounds in the presence of palladium(II) complex as catalyst which can be performed in mild reaction conditions. This review solely focused on the transition of innovation from palladium to other transition metals i.e. copper(I, II) and nickel(II), and emphasized on their catalytic capacity and mechanistic details. The optimization of reaction conditions is also reviewed in this paper by varying the types of bases, amounts of catalysts, temperatures and types of solvents. The catalytic optimization is essential because optimum reaction conditions directly influence the yield of product formed. This review also focused on the effect of aryl halides towards Stille reaction in which electron-withdrawing and electron-donating substituted aryl halides were converted to their corresponding biphenyl products by Stille reaction.