Synthesis of C3-sulfone substituted naphthols via rhodium(iii)-catalyzed annulation of sulfoxonium ylides with alkynylsulfones

Abstract

A sulfoxonium ylide directed C–H activation/alkynylsulfone annulation approach for the step-economical assembly of C3-sulfone substituted naphthols with high regioselectivity.

α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

“…The synthesis of sulfone-possessing naphthols 180 was reported by Zhu and coworkers 85 with high regioselectivity (Scheme 83). The reaction between sulfoxonium ylides and alkynylsulfones 179 in the presence of the Rh( iii )-catalyst and zinc triflate in DCE delivered the annulated products in good to moderate yields.…”

Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides

“… [33a] Recently, Zhu et al . reported a regioselective C3‐sulfone‐substituted naphthols by Rh(III)‐catalyzed annulation of sulfoxonium ylides with alkynylsulfones [33b] …”

Gold‐Catalyzed Oxygen Transfer to Alkynylsulfones: A Diazo‐Free Route to 4‐Sulfonyl‐1,3‐Oxazoles

“…[17,20] The relevant transformations of electron-deficient alkynes, which exhibit a significant inertness toward oxidation, are poorly studied; the reported examples include only alkynylcarbonyls such as propiolates or ynones. [21][22][23][24][25] Alkynylsulfones -electron-deficient alkynes bearing accepting sulfone fragments -were recognized as versatile reagents for alkynylations, [26][27][28][29] and, in addition, these species are also often used as building blocks in cycloadditions, [30][31][32][33] nucleophilic additions, [34,35] or coupling reactions. [36,37] We have recently shown that alkynylsulfones can be readily hydrated under gold-catalyzed conditions.…”

“…Alkynylsulfones – electron‐deficient alkynes bearing accepting sulfone fragments – were recognized as versatile reagents for alkynylations, [26–29] and, in addition, these species are also often used as building blocks in cycloadditions, [30–33] nucleophilic additions, [34,35] or coupling reactions [36,37] . We have recently shown that alkynylsulfones can be readily hydrated under gold‐catalyzed conditions [38] .…”