Cross-coupling of chloroarenes with boronic acids using a water-soluble nickel catalyst

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

“…In this regard, a watersoluble Ni(0) catalyst formed from NiCl 2 (dppe) and TPPTS was found to catalyse the cross-coupling reaction of a variety of aryl chlorides with arylboronic acids to afford good yields of biaryls (Scheme 30). 76 Additional studies indicated that the SM cross-coupling can be extended efficiently to a range of aryl bromides and arylboronic acids using a water-soluble Pd(0)/TPPTS catalyst under mild reaction conditions (Scheme 31). 77 This procedure has been extended to electron-rich and electron-poor substrates and provides an easy access to sterically hindered biaryls having three ortho-substituents with good ton.…”

Palladium Nanoparticles Supported on Polyaniline Nanofibers as a Semi‐Heterogeneous Catalyst in Water

“…[13][14][15][16] Another limitation of Suzuki coupling is that more economical aryl chlorides are less reactive than aryl bromides and iodides, and protocols for such reactions conducted in water are few. [17][18][19][20][21][22][23] Furthermore, Suzuki coupling catalyzed by other palladium nanoparticles [24,25] generally does not work with aryl chlorides. [26] Consequently, we first tested the Suzuki coupling between p-chlorobenzoic acid and phenylboronic acid in water.…”

Nickel‐Catalyzed Cross‐Coupling Reactions

“…Recently, cross-coupling with organoboranes has been optimized as being applicable for aryl chlorides (entries 1-5) [47][48][49][50][51][52] and aryl sulfonates (entries 6-10) [53][54][55][56][57], without any loss of efficiency. Compared with an aryl Grignard reagent, the reactivity of arylborane towards aryl chloride is different.…”