One-Step Synthesis of Acylborons from Acyl Chlorides through Copper-Catalyzed Borylation with Polystyrene-Supported PPh₃ Ligand

Abstract

We developed a one-step synthesis of acylborons from both readily available acyl chlorides and bis(pinacolato)diboron through copper(I)-catalyzed borylation. Under the reaction conditions using t BuOLi, polystyrene-supported triphenylphosphine as a copper ligand was found to promote the borylation of acyl chlorides while suppressing alcoholysis. This method enables the facile synthesis of potassium acyltrifluoroborates.

Copper‐Catalyzed Stereoselective Borylation and Palladium‐Catalyzed Stereospecific Cross‐Coupling to Give Aryl C‐Glycosides

“…PS‐PPh 3 was used in the Cu‐catalyzed borylation of alkyl halides by Liu [12a] and Molander [12b] for facile purification of the desired products to avoid the contamination of PPh 3 oxide. Meanwhile, we recently discovered that PS‐PPh 3 gave better yields than other phosphine and NHC ligands in the Cu‐catalyzed borylation of acyl chlorides by promoting borylation while suppressing the undesired alcoholysis of acyl chlorides [15] . Although the role of the polymer is not clear, the use of PS‐PPh 3 as the ligand in Cu‐catalyzed borylation reactions was found to be effective for the improvement of yield as well as facile separation.…”

Syntheses, characterizations and catalytic properties of three zinc complexes and one lithium compound chelated by β-diketiminate ligands

“…36,37 However, the reactions required noble metal catalysts, including Ir, 38,39 Rh, 40 and Pt. 41 Recently, Cu 42,43 and Zn 44,45 have been recognized as efficient surrogates of these noble metal catalysts. However, there are very few such compounds.…”