Sulfonyl motifs such as sulfones and sulfonamides play an important role in drug discovery. They are widely used as linkers between pharmacophores and play a role as isosteres for common functional groups. Until the recent development of palladium and copper catalyzed methods to access custom sulfonyl moieties, synthetic options were limited to utilizing commercial monomers or employing hazardous and intolerant reaction conditions. In an effort to expand the available synthetic space around these important functional groups, we have developed a novel gold(I)-catalyzed synthesis of sulfinate salts from aryl and heteroaryl boronic acid derivatives. A plausible catalytic cycle was described from stoichiometric reactions and selected mechanistic experiments. The sulfinate salts can be elaborated in situ to sulfonamides and sulfones in either singleton or library formats. The use of widely available boronic acids greatly increases the scope of products accessible with this methodology. In addition, this user-friendly catalytic process uses commercial reagents and catalysts and is not affected by air or moisture.                                                        

Development of a gold-catalyzed synthesis of aryl sulfinates: Access to sulfonamides and sulfones

248th National Meeting (2014)

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