Pd-Catalyzed Desulfitative Heck Coupling with Dioxygen as the Terminal Oxidant

Abstract

A Pd-catalyzed desulfitative Heck-type reaction of aromatic sulfinic acid sodium salts with various olefins is developed with O(2) as the terminal oxidant under mild conditions. The presence of phosphane ligand DPEphos in anisole can significantly enhance the reaction selectivity.

Direct Synthesis of Aryl Ketones by Palladium‐Catalyzed Desulfinative Addition of Sodium Sulfinates to Nitriles

“…[19] Recently, we developed a palladium-catalyzed desulfinative Heck-type reaction of aromatic sulfinic acid sodium salts with various olefins under mild conditions. [20] Herein, we report the direct synthesis of aryl ketones by palladium-catalyzed desulfinative addition of aryl sulfinic acid sodium salts to nitriles under mild conditions (Scheme 1).…”

Copper-catalysed Coupling of Aryl Tosylates with Sodium Arylsulfinates

“…The solvent for the coupling reactions was investigated carefully in order to uncover optimum reaction conditions (entries [11][12][13][14][15][16][17][18][19][20]. Reactions conducted in various organic solvents occurred in low yield with [Cu(CH 3 CN) 4 ]PF 6 under 120 °C, possibly due to the poor solubility of sodium phenylsulfinate in the solvent (entries [11][12][13][14][15][16]. Specifically, aprotic polar solvents lead to a much higher yield compared to other solvents (entries [17][18][19].…”

Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base

“…All compounds are determined by MS analysis and obtained results were compared with these published in the references [70][71][72][73][74][75][76][77][78][79][80][81][82]. …”