Microwave-Assisted Palladium(II)-Catalyzed Synthesis of Aryl Ketones from Aryl Sulfinates and Direct ESI-MS Studies Thereof

Abstract

A fast palladium(II)-catalyzed and microwavepromoted procedure using 6-methyl-2,2 0 -bipyridyl as ligand to synthesize aryl ketones from aryl sulfinates and nitriles is described. More importantly, the first detailed investigation of the reaction mechanism using direct ESI-MS studies is reported.

Copper-catalysed Coupling of Aryl Tosylates with Sodium Arylsulfinates

“…None of the desired products have been detected without a copper catalyst (entry 10). 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].…”

Synthesis of Symmetrical Diaryl Sulfone by Homocoupling of Sodium Arylsulfinate

“…The organic phases were evaporated under reduced pressure and the residue was subjected to flash column chromatography (silica gel, ethyl acetate/petroleum ether = 1/10) to obtain the desired product. All products are known compounds and were characterised by 1 H NMR, 13 …”

“…Sodium arylsulfinate has emerged as a new coupling reagent in Pd-catalysed desulfitative C-H activation and cross-coupling. [8][9][10][11][12][13][14][15][16][17][18][19][20] Sodium arylsulfinate has also been used as an aryl sulfonyl reagent to provide sulfone groups by crosscoupling with aromatic halides [21][22][23][24][25] (Fig. 1A) and aryl boronic acids [26][27][28][29][30][31] (Fig.…”

“…J = 8.0 Hz, 4H), 7.40 (d, J = 8.0 Hz, 4H);13 C NMR (100 MHz, CDCl 3 ): δ 138.9, 137.8, 128.0, 126.4. HRMS calcd for C 12 H 8 Br 2 O 2 S: 373.8612, found: 373.8617.…”

Pd‐catalyzed Desulfitative reaction of Aryltrifluoroborates with sodium Arenesulfinates in water

“…In recent years, the readily accessible sodium arylsulfinates have attracted considerable attention in organic synthesis as precursors in various cross-coupling reactions due to the easy availability and the compatibility with numerous functional groups. Interestingly, sodium arylsulfinates were also reported as the coupling partners for the Pd-catalyzed desulfitative coupling reactions, such as desulfinative Heck-type, [36][37][38] addition reactions to double or triple bonds, [39][40][41][42][43] as well as cross-coupling [44][45][46][47][48][49] and C-H arylation [50][51][52][53][54][55][56][57][58][59] reactions have been well developed. [60] Moreover, the related reaction conditions were found much milder than those reported for the corresponding aryl carboxylic acids.…”