Synthesis of Sulfones via Ru(II)-Catalyzed Sulfination of Boronic Acids

Abstract

Ruthenium(II) complexes catalyze the insertion of sulfur dioxide into (het)aryl and alkenyl boronic acids. The transmetalation−sulfination process proceeds with DABSO in the presence of 5 mol % RuCl 2 (PPh 3 ) 3 in methanol at 100 °C. The intermediate sulfinate salt can be quenched with various electrophiles such as alkyl halides, epoxides, Michael acceptors, and λ 3 -iodanes in moderate to good yields. The reported sulfone synthesis can be performed either as a direct one-pot or one-pot twostep procedure depending on the reactivity of the electrophile.

DABSO as a SO2 gas surrogate in the synthesis of organic structures

“…As shown in Scheme 24, a one-pot reaction of aryl iodides, aryl boronic acids, and DABSO leads to the formation of diaryl sulfones in the presence of Cu(I) salt as the catalyst in N,N′-dimethylpropyleneurea (DMPU) as a polar aprotic solvent. 61 In another research study, Ni(II), 62 Ru (II), 63 and Cu(II) [64][65][66] catalytic systems were employed to access similar products.…”

DABSO – A Reagent to Revolutionize Organosulfur Chemistry

“…Similarly, the use of ruthenium(II) catalysts was demonstrated by Turks and Gulbe for the synthesis of aryl sulfinates and their derivatives. 51…”

Recent Advances in the Catalytic Synthesis of Arylsulfonyl Compounds

“…Recently, the Turks group employed a ruthenium catalyst for the assembly of various sulfones from aryl boronic acids and alkyl halides with DABSO as the sulfur dioxide surrogate (Scheme 102). 164 The method exhibits good functional group tolerance and is applicable to a gram-scale synthesis.…”