Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives.

An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium -butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO ) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite™ and TBSCl, serves as a potent nucleophile in -alkylation and Cu-catalyzed -arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.