Suzuki cross-coupling reactions of aryl halides in phosphonium salt ionic liquid under mild conditions

Abstract

The Suzuki cross-coupling of aryl boronic acids with aryl halides, including aryl chlorides, proceeds in the phosphonium salt ionic liquid tetradecyltrihexylphosphonium chloride under mild conditions.

Ionic Liquids: The Synergistic Catalytic Effect in the Synthesis of Cyclic Carbonates

“…Cycloaddition reactions were carried out at 100 °C and 1. Phosphonium halides are more thermally stable [61][62][63][64][65][66] when compared with the ammonium halides. Moreover, they could be separated easily from the products since they have little potential interaction with the products [67].…”

Ionic liquids: a versatile medium for palladium-catalyzed reactions

“…119 The reaction proceeded well in THPC using various mild bases but potassium phosphate and water (added for salt solubility) were found to be the best base for this system. Addition of small amount of toluene helped in complete solubility of both the boronic acid and aryl halide in the ionic liquid.…”

“…Complete conversion of aryl iodides, bromides and even in case of electron deficient chlorides in the THPC at 50-70 °C was achieved, indicating that a very active catalyst was produced in the THPC system. 119 This catalytic system can be reused for many times, indicates that the catalytic system is highly stable in the reaction conditions.…”

Quaternary Ammonium and Phosphonium Ionic Liquids in Chemical and Environmental Engineering

“…Another interesting example is the use of ILs in Suzuki cross-coupling reactions (carboncarbon bond formation between an sp 3 carbon or non--hydride containing electrophile and a boronic acid derivative; Miyaura & Suzuki, 1995). Cyphos ® IL 101 has been recently reported as an extremely successful medium for such types of reaction (see Figure 7, McNulty et al, 2002). The palladium catalyst (Pd 2 (dba) 3 CHCl 3 ) was dissolved in the IL, forming a stable solution in absence of oxygen, and hence could also be effectively recycled after solvent extraction of reaction products.…”